#49 How They Built It: REACTIV - Lessons in Risk, Reward, and Entrepreneurship | Ryan Boykin, Founder & CEO

Ryan Boykin is Cofounder and Partner at Atlas Real Estate and Cofounder of REACTIV. In part one of this episode, Ryan and Daniel discuss risk, reward, and entrepreneurship.
Last updated
August 14, 2023
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Ryan Boykin has purchased over 7,000 units of investment real estate in the last 10 years.
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#49 How They Built It: REACTIV - Lessons in Risk, Reward, and Entrepreneurship | Ryan Boykin, Founder & CEO

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“You have to start businesses with an eye towards what they will become, but also an eye towards some of the risk associated with it. And a two-miracle deal requires way too much risk, and you've got to walk away from those before you start them.” – Ryan Boykin

Ryan Boykin (@atlasrealestate) is Cofounder and Partner at Atlas Real Estate, a full-service real estate firm that manages more than 3,400 units. He is also Cofounder of REACTIV, a platform that simplifies commercial real estate transactions. Ryan has written or been featured in many publications, including Bloomberg, The Wall Street Journal, and Investopedia. He was chosen for Denver Business Journal’s 40 under 40 list in 2017.

To listen to Ryan’s bonus interview and learn more about the habits and tools that help him focus, click here.

Chapters in Part 1 of this interview:

  • Ryan’s thoughts on business as a problem solver
  • What makes a person an entrepreneur
  • How Atlas Real Estate and REACTIV began
  • On risk, reward, and overcoming negativity
  • Overcoming fear
  • Building for the long-term
  • Advice for entrepreneurs
  • Reflection and self-care
  • Entrepreneurs: just do it!

Links from Part 1

Books Recommended by Ryan Boykin

Learn More About This Topic

Power vs. Force: The Hidden Determinants of Human Behavior by David R. Hawkins

One of Ryan’s recent reads that had a profound impact on him, about the connection between individual levels of consciousness and human behavior.


You Are the Placebo: Making Your Mind Matter by Joe Dispenza

Another of Ryan’s recent reads about using the mind to heal the body.


The Big Short

This Oscar-winning film focuses on the collapse of the housing bubble in 2007 and 2008.


14 Important Factors Impacting Commercial Real Estate in 2021 and Beyond – Forbes

A timely look at the commercial real estate industry that REACTIV is preparing for.


Explaining Rising Interest Rates and Real Estate to Clients – Investopedia

This piece, authored by Ryan, gives a great overview of how investors can navigate fluctuating housing prices.

Transcript

Daniel Scrivner:

Ryan Boykin, welcome to Outlier Academy.


Ryan Boykin:

Thank you. It's great to be here.


Daniel Scrivner:

I've been looking forward to this conversation for an incredibly long time. We've been talking about this for a while. We had a call to map out what we're going to discuss awhile ago, and this has been on my mind for a long time. And the umbrella I was thinking about this conversation underneath is, lessons and risk-reward in entrepreneurship, and using that to explore your journey as well as a bunch of the things you've learned throughout the course of your life and your career so far.


Daniel Scrivner:

And I typically ask a really different starting question, which is to share your background, but since today we're going to go through that in detail and extrapolate out a bunch of things to learn, I want to start with a very different question, which is, when you're asked what do you do, what is your answer?


Ryan Boykin:

Oh man, what a great start. I almost don't even want to give an answer because I feel like it'll take so long to explain. We spend so much time in all of our companies talking about our elevator pitch and how you get somebody captivated in a 15-second comment and how you get them to ask a question, and I've got to really learn to practice what I preach. What I do is I start businesses, and they've ranged across many different fields and industries. And I think that if you map these different businesses on a piece of paper, you'd say, "What does this one have to do with this one? Or this one have to do with this one?"


Ryan Boykin:

And really, when I look at it, I start businesses that do two things, I hope. The first one is, I think that business is the best vehicle that our world knows to utilize to solve big problems. And my greatest motivation is to use business to solve problems. And then I think that when you retrench on capitalism and the marketplace that we participate in, I try to identify businesses where the cards are weighted in my favor so that I have a chance for success. One of my oldest mentors said to me 15 years ago, "Every new business that you ever start requires a miracle to have success." And I could just not agree with that any more. It is just so tough.


Ryan Boykin:

And he also said, "Make sure you never start a business that requires two miracles. If you have a two-miracle deal, just kill it on day one." And that's to say that you have to start businesses with an eye towards what they will become, but also an eye towards some of the risk associated with it. And a two-miracle deal requires way too much risk, and you've got to walk away from those before you start them.


Daniel Scrivner:

It's fascinating. That first part of your answer, I would love to explore a little bit more because I've thought about that many times, and I think that I agree with you. I think that businesses are an incredible tool to solve some of the biggest problems we face. I also think that's really controversial and we live in a time where a lot of people would push back on that. Why do you think that's the case, and why do you think other tools just aren't able to achieve the same impact or same effect?


Ryan Boykin:

Sadly, we're living in a moment, no matter what you say, it can be controversial to somebody. And I think even before I answer your question, I just want to lean into this moment of saying that when I choose to perceive the world as tough, the world reflects itself to me as tough, and when I choose to perceive the world as beautiful and positive, I realize that I am surrounded by positivity in every little corner of my life, and that that is my human experience. And I choose to participate in that field a little bit more. So that's a commentary that's less about the business and more about how we see the world.


Ryan Boykin:

My commentary about business being the best vehicle through which we can solve problems and actually ultimately change the world really just comes down to, our world is governed by business, it's governed by capitalism, it's governed by the flow of our economy. And if I'm able to do something that can make money and at the same time serve every single stakeholder that touches it, and at the same time, do something good for the planet, do something good for our environment, then everybody else is going to see that. And because I have a little success on it in this little measured way that we call money and profitability, the whole world will copy it. And in copying it, we're actually raising the bar, we're making the world a better place.


Ryan Boykin:

And so my notion behind it is that if we can do something good and people then see that and replicate it, then that's okay. And really, business is sustainable. The nonprofit world, the religious sector, governmental, it requires constant feed and constant fuel for the system to continue to turn. Profitability, while it can be really tough if not administered correctly, also ensures that something is sustainable and can survive. We all have to check the survival box before we can figure out what we really care about in life, and business enables us to survive so that we can really become good stewards and serve.


Daniel Scrivner:

I love that definition. I could listen to you expand on that for another 30 plus minutes. And I think that's the right definition of business, the one that you define there where it's not only about ideally being sustainable, which means being profitable, that's the only way you're sustainable, but it also means serving all the stakeholders in that business. And I think that if that was the common definition that most people pursued, most people thought about as business, that maybe business would be perceived better. But I think a lot of people perceive it as extortionist or, I don't know, if you've been able to achieve success, you've done something wrong, and I don't think that's the case at all.


Daniel Scrivner:

Another thing I like about business too is, business is inherently about skin in the game. You have to take risk in order to launch something. You have to put capital at work in order to grow a business. And there's something really reciprocal and aligned with nature about that. I'm curious how you think about and define an entrepreneur. So if that's maybe how you think about a business, what is an entrepreneur? Or maybe if you don't want to define it, how do you think about what it entails to be an entrepreneur?


Ryan Boykin:

I don't know that I'd be the best person to define an entrepreneur, but there's a couple thoughts that come to mind when you share that with me. The first one is that, in the American society today that I've experienced, I don't think that we're really trained all that much to be entrepreneurs anymore. We're told to go to school and get a good grade and go to college and get a job and go take on some debt and pay down the debt and buy a house. All of those things are amazing because they're a defined pathway that is quite certain. If you do those things, you're going to check your survival box, you're going to be okay.


Ryan Boykin:

My survival box, my definition of what it looked like to survive was just a little bit different because I want to experience this lifetime. And entrepreneurship was a pathway for me to be able to survive financially, to be able to survive with my relationships by investing deeply into my relationships inside of my business and outside of my business. And those things ensured at a much greater level my survival than the certainty of a paycheck. And I can't emphasize enough. There was about a decade there or so where I wasn't really surviving financially, but had I compared my journey to any of my other peers, I would've never traded it because I was thriving as a vibrant human, I was alive, I was experiencing, consuming this thing we called life.


Ryan Boykin:

And being an entrepreneur put me at the front seat of that roller coaster ride. And that's something I couldn't have traded. And it's also something that financially, I was very willing to sacrifice financial gain in those moments because I was much more motivated by those other pillars or those other elements of our life. But being an entrepreneur is all about taking risk. And I think it's also all about asking yourself what's broken or where there's a problem in this life and where you see need, you get to be that inventor as it were. I'm not smart enough to be an inventor, I'm not smart enough to be the mad scientist, I'm just smart enough to see something that is formless and see if I can cobble together a couple of ideas to turn it into something real.


Ryan Boykin:

And in that sense, I've always wanted to be a builder, but I don't build with physical products all that much, I realized that I build with humans on these things that we call businesses. And so, entrepreneurship for me is about taking a risk and it's also about having to consume life fully.


Daniel Scrivner:

That's an incredible definition. I'd love to go back and walk through your journey. And there's a lot to explore there. You started out into stressed assets, we'll talk about that, you then moved into operating companies, and now you're building a technology business, which is much more venture capital. And so you've gone through this really interesting progression. And I thought it would be worthwhile to explore each of those. And the first one is very different, at least my take. It's much more about investing and putting capital at work where you saw an opportunity and where there was also a lot of risk.


Daniel Scrivner:

And I don't want to give away the story, so maybe I'll just tee up. If you could take us back into time, can you describe what you were seeing, the opportunity that you saw and how you ended up capitalizing on that?


Ryan Boykin:

You bet. I think that probably where the story begins as it relates to this conversation is 2008 with the financial and subprime foreclosure collapse that we all experienced. I had come out of a different field, a different entrepreneurial vision and journey prior to that. And it's never bad to realize where you got lucky. I had sold my prior business just prior to Lehman's collapse a few months before that, in early 2008. And I surveyed the field thereafter and it looked like basically everything in business was broken and, what the hell was I going to do with my life? I had a little bit of money, but not enough money to make anything really work.


Ryan Boykin:

And the one thing that occurred to me was real estate was on sale. And we've all heard the adage, "Real estate is the only thing that goes on sale that people don't buy." And somewhere along that I said, "It probably makes sense when I can buy this physical product, probably cost $100 to build or $100,000 dollars to build, pick a number, and I can buy it for $25,000." How often can you buy something that costs 25% of its cost to build? Those moments in time I think are quite rare. And what's difficult is if you listened to the noise, then you only saw the world as being negative.


Ryan Boykin:

If you really listened to the media and the noise, everything was falling apart and it was a collapse and it was the end of the system. But if you stepped back and you surveyed your own experience, and I was really fortunate somehow to be able to step and say, "Gosh, my experience is, people still want to go to work. My experience is, people still need to have a roof over their head, and that's the starting point of their journey towards personal fulfillment, is their community, their home." And so I gathered a little bit of my own money and I raised some money for some other people and we started buying real estate at foreclosure sale. And we bought thousands of properties of real estate starting with single family.


Ryan Boykin:

And this is the most humble beginnings ever, Daniel. We were a fix and flip company. We did maybe 500 fix and flips in our first year of business buying them for $1 over the asking price of foreclosure sale. And I made every mistake in the book, and contractors stole money from me, and business partners that didn't work out. But along the way, the cards were waited in my favor. I was able to get my education in real estate. And rarely in life do we get to get an education and get paid to get that education. Rarely in life do we get paid to get that education. Mostly, we have to pay someone else.


Ryan Boykin:

I go to Stanford, I'm going to pay them a few hundred thousand dollars for my education. In this situation, despite all of our mistakes, we still were able to make some money. And then we continued to buy real estate. And from 2009, until about 2013 or '14, we bought all sorts of single family, multifamily, office, industrial, retail, you name it. Every kind of real estate you can imagine, we bought it at bargain basement prices, and we did a big value add. And I still own that real estate portfolio today. Everything that I do is very long-term oriented. So I still own all that real estate. And it continued until we had an opportunity to build a business outside of that but still in the real estate sector.


Ryan Boykin:

And that came to my second moment in founding another different type of business. So the first iteration from 2008 to about 2013 was all about buying assets. Then in 2013 or 2014, it occurred to me that real estate prices were skyrocketing to the north. And I didn't quite read the tea leaves perfectly because had I continued to buy aggressively in 2014 and '13 on through to today, I would've captured a lot more appreciation and I would've captured a lot of upside on my real estate. But from my vantage point, I was saying, "This real estate looks a lot more expensive than it did a few years ago. Maybe it costs $200 a foot to build this real estate and now I can only buy it for $180, or maybe I have to pay more than the actual construction cost."


Ryan Boykin:

And so I started to say, "I think that I can still make some more money buying real estate, but I think that I'm also not reducing my risk. I think the cards aren't weighted in my favor as much." And I have this other occurrence or thought process, which was, "I'm also not that motivated by just making money." And if I just wanted to make money in my life, which I enjoy doing, and it is a motivator for me, then I would keep on building this great real estate portfolio and just playing that game. Instead, I wanted to start to solve some problems. And for my personal journey, I realized that in so much as I had checked my own survival box in my life, that just reduced the amount of motivation I found in just making more money.


Ryan Boykin:

And instead, my motivations came to solving problems and my other main motivation in life is really developing very deep, meaningful relationships in my life. So then I asked myself, "What's a problem that I can solve?" And the one problem that I [inaudible 00:13:36] upon was this difficulty that I think many people have of how they're going to retire one day. We're in a moment where we don't have pension funds, 401(k)s don't work particularly well, people are going to have many jobs over many different careers and positions. And if you ask the common Joe how they're doing and saving for retirement, heck, I think 50% of all baby boomers have less than $100,000 in the bank for savings for retirement.


Ryan Boykin:

So at that moment I said, "Geez, I think I have a solution for this." And my solution was buy a rental property. Keep it really simple. If I go and I talk to you, Daniel, and I have you buy one single piece of rental real estate and you of that for 20 or 30 years, it'll be paid off. And probably when you become retirement age, it'll be worth three times more than what you buy it for now and it'll pay you a nice passive income. And imagine if we can do two or three or four of those, you're going to retire. And so what we did is we said, "Let's take our learnings from owning real estate ourselves, and let's take our learnings from having property managed all of our own real estate across five different states and thousands of doors, and let's share it with people so that we can teach them how to do this."


Ryan Boykin:

And that's when Atlas Real Estate was born. And today, Atlas Real Estate is a great company. We're a real operating company. We help people to buy investment properties. We help people to make them passive by doing the property management for them, and we also have an investment arm that's paired with some pension funds to help them get return on investment in the single family real estate sector. And we did that at a good moment because it was something that nobody was doing, and because nobody was doing it, we could outperform the competition. And we really aligned interests among the stakeholders, the owners that own the property and the tenants that are in the building as residents, etc.


Ryan Boykin:

And we got that machine working, and Atlas is still working and it's a beautiful company and it's got a life of its own. And about a year and a half ago, I said, "Geez, I'm ready to go start something new and go be an entrepreneur again." And so today, my final business that I'll comment on is REACTIV. And REACTIV is a PropTech company. So we're a technology company. That's all about solving the problem of the difficulty of leasing commercial real estate. So cut shortly, if you've ever leased commercial real estate before, it probably was a very complex, long, arduous process. And the rest of our society in all of our industries today is, click the button and receive the good.


Ryan Boykin:

And so, how do we make commercial real estate simpler for the prime purpose of inviting the entrepreneur, of democratizing commercial real estate to enable small business and growing businesses to thrive more quickly and pull down a barrier? Through one of my own personal experiences of being an entrepreneur, how do we make that an easier journey? Because truthfully it's a very, very difficult journey. And when we can eliminate one of those barriers, we have an opportunity to ensure that America's still a great place by having great small businesses and young companies build within this beautiful Petri dish. So this is a techenable platform for commercial real estate leasing.


Daniel Scrivner:

That was an incredible description in a couple of hops, all the way back from 2008 to '10, I guess 12, 13 plus years forward in the future. I want to go back and explore Atlas and REACTIV in a little bit more detail. But before we do that, I have to go all the way back to 2008, because I wanted to explore a few things. And one of those is this notion of risk reward and how you were able to be in a place where emotions didn't color your decision making and you were able to see the opportunity and seize on it. There's a bunch of different things we can explore there. But I'm curious, when you were, I guess, considering that investment, were you ever scared about losing capital or in your mind, was that just not even a thing and you just saw the opportunity?


Ryan Boykin:

Yeah, I was scared as hell. Somebody asked me recently what I think I'm good at in business, and I'm frankly not the smartest guy in the room. I have a good head of my shoulders, but I'm not the smartest guy in the room. I basically chalk it up to two things. One is that I work really hard. People cannot work me for sure, but it's going to be tough. And that's important because when you make these mistakes and you buy the wrong deal and the world is collapsing around you, sometimes you sit back and you say, "The only resource I have is hard work to dig myself out of this." So that was one thing that saved me in those moments. But the other thing that I do think I'm a little bit good at is, I do have an ability to assess risk and reward.


Ryan Boykin:

Generally, as humans, we fall on one side of that spectrum, quite far on one side of that spectrum or the other. You meet somebody and all they see is the risk in the deal. And that person generally will spend hours and hours and hours vetting the deal and they'll see every angle. But frankly, they suffer from paralysis by analysis and they never make the bet because they can only see the risk, even though they can also see all the reward. And then you have the other person that says, "Every deal's going to be a unicorn and a billion dollars." And all they see is the reward. They don't ever see any of the risk.


Ryan Boykin:

I think it's actually a little bit rare and it's something that we're not trained and we're not taught that somebody can actually see the risk and the reward and assess them. So I knew every time that we were buying a property, that we might lose our money, but I also knew that the cards were weighted in my favor, and if I was able to get enough bats at play, eventually I would hit some balls. And as it turned out, we hit almost every ball because the moment was so good. In retrospect, I probably could have been riskier, I probably could have doubled down, I probably could have done two or three or four times more than what I actually did. That would've been the wise thing to do.


Ryan Boykin:

So sometimes I say, "I'm kicking myself for not having gone deeper in that moment." Now, the converse of it is, there were so many moments that we thought that the world was actually collapsing. And in those moments, it's really hard to stare that in the eye and still move forward. I do think that both in this moment right now, when we're in a moment of exuberance, for many reasons, pandemic aside, as well as in the moment of complete despair of 2008, those are both potentially bubbles. And what happens in a bubble is they feed themselves. One is a bubble up and the other is a bubble down, but when they're feeding themselves, they're self-fulfilling prophecies.


Ryan Boykin:

And so we have to realize, "Okay, take a step away from that. This is the human propaganda building this either up or down, and how do we see the force of the trees a little bit?" But we made a lot of mistakes along the way. And I got bailed out by a market that recovered. And had it not recovered, I might be sitting in a very different chair right now.


Daniel Scrivner:

Yeah. Two things seem very related with you, the idea to see risk and reward and be able toggle between those two and ultimately make a decision, which I think you're right. On either into that spectrum, but especially if you're are overweighted on risk, you just never make any calls and you never make any calls that have any risk in them, which is totally doesn't make any sense. And then this other notion of just making sure that the cards are stacked in your favor, because if you do then it's almost like that concept of margin of safety. I want to go back to something else you said, and it's something I think about a lot, because I feel like it's a very common experience of just be in a moment where the news around something is overwhelmingly negative, where the takeaway, if you were to read all the headlines and just turn off your brain and just conclude what everyone was telling you, is that everything is terrible, it's going to zero, it's never going to recover, this is completely done.


Daniel Scrivner:

And I guess my thoughts on that, it has led me to, one, just really disconnect from news and try to be very selective about how I engage with it, but the other is this idea that when that's true, when stuff reaches a fever pitch of negativity, that's often the best time to invest. And so I'm curious, what are your thoughts, what are your conclusions, what your insights about how to handle overwhelmingly negative news or moments? And then, what does that signal to you or what does that lead you to do or lead you to think?


Ryan Boykin:

You know what, Daniel, my first thought on this is that we don't spend enough time studying ourselves. And let me go deeper on that. In recent years, I've come to realize as I've studied myself and as I've had real self-reflection, I found that surrounding myself with news and surrounding myself with negativity is literally the worst food I could ever put in my body for myself. I wouldn't eat candy all day, and that's what I'm doing. And so why do I subject myself to that? Well, I subject myself it because there's this pressure to be up to speed every second. And we get that pressure at every turn the second we wake up, the notifications, the talking to people around the water cooler, you name it.


Ryan Boykin:

I don't read any national news. It's completely off. I'm not in any social media whatsoever. And you know what? Sometimes somebody says something and I had no idea was happening, and I'm just like, "Ah, damn, I wish I would've known that. I kind of look like an idiot right now." I'm willing to take that one or two times every year when I miss something that I wish I would've known about in exchange for the other 363 days of the year that are filled with complete positivity briming to the top based on what I do choose to surround myself with. And we are a product of what we surround ourselves with, we are what we eat.


Ryan Boykin:

And so for me, that's how I define fulfillment, that's how I define how I will thrive as a human. Now, others may not thrive under that dichotomy. I think what's important is that we truly search and understand ask ourselves how I'm actually going to be the best human that I can be. And so that's my starting point on this, and that's why I don't surround myself with that so much. I think that sometimes when you're about to make a bet, just to make it simple, when I make a bet, that's starting a new business, and it's a giant bet for me. I'll invest a ton of my own money into it, I'm going to ask other people I know potentially to invest in it with me, and I have tons of reputational risk on that.


Ryan Boykin:

And I'll tell you, I've never lost more or sleep in my life knowing that I might lose somebody else's money. Losing my own money, I almost am like, "Eh, that's going to happen. I can confront that brutal fact." Losing somebody else's, that is some stress for me. And then on top of that, when I make a bet, I'm going to spend minimum five years of my life on this bet. We have one commodity in our life and it's our time. So in those moments, when I'm about to engage on something and I'm truly, truly assessing risk and reward, I'm spending a lot of time researching and going down the vortex and speaking to people and trying to peel back the layers, the initial layer that's covered in social media and media and all the things that we see on the surface to try to get deeper to see what the actual experience is so that I hope that I'm coming to conclusion points that can help direct me.


Ryan Boykin:

In those seminal moments, I'm definitely going deeper to make sure that my conclusion point is accurate. And I think in the moments, I try to turn down the noise a little bit.


Daniel Scrivner:

Yeah. I think that's super interesting. That makes a lot of sense. And I love that with all these points, you continue to bubble it up to some meta idea, which is much more powerful than just engaging or framing it as news versus no news or negativity versus no negativity. I want to ask one more question and anyone that's had quite a bit of success and a number of instances at bat has plenty of hindsight 20/20 moments where they kick themselves in the butt because that's part of life, you're never going to understand or take all of the turns you "should have taken."


Daniel Scrivner:

You made a comment talking about you started investing 2008, 2009. You saw prices zooming up in 2013, 2014, and you could have gone much further. And that's something that I've thought about and I know anyone that's an investor struggles with, I guess to bubble that up, the idea would be say, there was a crash you got in at the crash, now things are starting to accelerate up, do you push it? Do you continue to keep investing? And so the question I wanted to ask you there was, you said that you could have doubled down, but you didn't, so clearly, there's an observation there. When you heart of heart, what is your takeaway?


Daniel Scrivner:

Do you think that you made the exact right decision in the time? Do you think that you should have been investing all the way until the moment where the market cycle turns over? Has that changed any of how you approach that?


Ryan Boykin:

I think that when I reflect back on that time period, what I was asking myself is, what type of company do we want to be? Is my opus going to be that I'm a real estate company and I'm going to figure out how to be a real estate company at all times, up market, down market, sideways, you name it, and that we're going to be a real estate company that's a developer, we're going to be a real estate company that is a true long term, passive cash flow core offering, we're going to have a fund or fund to funds? If that would've been my longterm vision as the thing that I wanted to do in life, then sure, I could look back at that moment and say, "I had all the tools at my disposal like nobody else in their business ever has with an IRR that's irrepricable."


Ryan Boykin:

But that's not what motivates me. And frankly, I still am doing that because we have businesses that are ongoing, that are living. These businesses are way bigger than I am, way bigger. And that was my goal, was to create something that was bigger than me, and that something had to be good for you, good for me, and good for everything. And if I could do that, that was my goal. And so I just didn't want to stop by just defining it as real estate. I talked about the value of time, I wanted to enable this possibility that my time could also be used to create another something beautiful, and that beautiful thing could also be bigger than me, and could serve more people, and could be something good for the planet.


Ryan Boykin:

So I definitely don't have regret with the pathway that we took. Sometimes you have to look via different lenses. And if my goal was just to make money, then maybe that would've been the best pathway. My goal isn't just to make money. And who's to say that I didn't make more doing it this way? I have no idea. But that just isn't my measuring stick. I will also not be so Pollyannish to say that it's not a measuring stick. I'm in the capitalist world, I want to use that as a measuring stick, but I don't think it's the primary or even the secondary, there are many others that are much more important to me.


Ryan Boykin:

And by the way, one last thing, Daniel, this has been the funnest journey on the damn planet. To say that I would've done something different, the days that I was beat down, crying my eyes out on the floor, couldn't pay the mortgage, I wouldn't trade them. I want to live, I want experience, I want to eat this terrible, hard challenge and then get up from it and say, "We made it through another battle." That's who I am.


Daniel Scrivner:

It's much more about the progression and the evolution rather than just optimization. And I think that that's super interesting. For you, it's like you're okay to stop pursuing a certain opportunity to pursue a new one, take that leap of faith. I think this speaks to a lot of things, because I know people who could be plenty successful in five different fields, but they stay in one field because it's like, "Here it is. I've got it. I can't give it up. I don't want to lose it." And it's this very fear-based mentality. Is that how you think about that and so that enables you to be really comfortable taking that leap to the next thing?


Ryan Boykin:

Yeah. I think that actually something for those people and something for myself that I've discovered is that in those moments where I've got something working and I'm like, "Ah, why would I ever leave this? This is working. I've got it all here." One of the things that I've come to realize, and I give an amazing credit to the CEO of Atlas Real Estate, Tony Julianelle, hey, there's probably somebody better than me at doing this. This company could be 3X or 5X better in serving the humans that it touches if I get outta the way. That's the coolest thing ever. The company could be stronger if I have a different role, a smaller role.


Ryan Boykin:

Who's the next person to be the leader of this? And how do we ensure that we develop those other future leaders through all the different caveats and corners of the business? And then, how do we get even more mission driven to be able to help a resident to purchase a home one day so they can actually have a chance at financial security? To help my parents' generation to figure out how they're not going to be destitute when they're 70 and 80 years old because they don't have the money in the bank. So I think that viewed under a different lens, that conversation becomes quite easy, and I think that the battling point becomes our ego.


Ryan Boykin:

And I've had to have that battle and I haven't resolved it. I don't know what human that I've met has resolved it. I'm grateful for the battle though, because as I reflect introspectively, I realize, "Hey, I have some other good that I can express and try and I have a better opportunity to have success with it because I'm at survival and because I have more resources at my disposal and there's actually more cards weighted in my favor at this stage than they were when I was younger.


Daniel Scrivner:

I want to ask one more question and then we'll move on. For the distress asset piece, you made a note and we've talked a little bit about just how successful that string of investments and distressed assets was, distressed real estate. But what I want to ask specifically is, you ultimately were able to be incredibly successful, print a really, really high IRR. I think what I've noticed is, when that happens, one, what that means is you are almost 100% certain to never hit that level of IRR again. And if you're an investor, that can feed in your mind. And two, and I think why that's difficult is, one, it's because it's the world and the results and just life pointing at luck, pointing at timing and not pointing at you, and that's hard to take.


Daniel Scrivner:

But then the other is just this idea that you ultimately then have to get over that notion that your goal is just to make more and more successful investments at higher and higher returns, which isn't a reality. And so the question I want to ask you is, was it difficult for you to get over that? Do you wrestle over, "Oh, I'm not making the returns I made then"? Just how do you not have this be this charge thing after that amount of success?


Ryan Boykin:

Two thoughts on that. The first one is it's always tricky to deal in absolutes and we'll never have that IRR again. Who knows? If you were a Bitcoin investor over the last couple years, you had way better IRR. And I don't understand that world, that world to me is speculation. I've got lucky with it a little bit because of some friend that understands it better, but we just don't know what the future will bring. And so maybe there will be those golden moments again. I do agree, I was completely lucky to be in a moment where I could make a bet, I was young, I didn't have too much to lose, I wasn't too jaded by prior experience. There was a lot of luck in that story.


Ryan Boykin:

The second component to your question is one that I definitely struggled with. There was a lot of deals that I didn't buy because they weren't as good as the ones before. But if you put them on the table right now, people would run over each other trying to get them. I think actually there was an investor that I really enjoy Howard Marks and he said this best, and it actually was the seminal changing point to my ability to view the investment world a little bit differently. He said, and this was recently that he said it, "We're in a low-yield environment. And when you're in a low-yield environment, you need to expect a low-yield return. When you're in a high-yield environment, you can expect a higher-yield return. And if you ever see those two things not matching, then that's an early indicator that you're taking on too much risk or you're over-weighing too much reward.


Ryan Boykin:

And so in a low interest rate environment like we're in, we're going to have lower yield. And that's the investment environment that we're in. So become more comfortable with it because of that. It's another way of saying, when we have more certainty in the system, then we're going to have a lower return. When there's higher uncertainty in the system, then we should expect higher return. And that's a good way of assessing risk and reward. That was pretty well put in that way and help to put my mind at ease on that. Then the other thing is that I'm a very, very long-term oriented person. When I build a business, I think about it over a decade or longer. Atlas, I hope last decades and decades.


Ryan Boykin:

My real estate, I know I'll own for 20 or 30 years. REACTIV is a little bit more unique in terms of the approach that we're taking and maybe it'll be a little bit shorter timeframe, but I'm very long-term oriented. Well, if you're long-term oriented and you sit back and you just get a 10% IRR every year for 10 or 15 or 20 years, forget about it, it's a ton of money. People get so IRR focused. And because you're so IRR focused, you get these giant IRRs, but then your money sits on the sideline for a period of time as well and you have to take more risk to do it. Well, if I'm getting a very low risk, 10, 12, 15% IRR, that is an irrepricable return in many respects. And I can do it for a decade, that's very achievable, even today in real estate.


Ryan Boykin:

Part of that is because we're in a low interest rate environment on the debt that you can procure, and so it's important to realize that, but if I can get fixed long term debt, cheap, fixed longterm debt next to rents in an appreciating rent environment, in an appreciating asset environment, that's going to work out really favorably for me over the long term. And that's essentially what we teach people at Atlas.


Daniel Scrivner:

I want to continue on and compare and contrast your or experiences and try to pull out secrets, insights, interesting things. One thing you've touched on a number of times is just being long-term oriented. And I know from your track record, I know from talking with you, that that seems to be something that's like very deeply rooted in your value system. And that's something that I think is very peculiar, because I know almost no one that doesn't say they're long-term oriented, but 99.9% of those people, when you actually compare their actions to their words, they're not at all long-term oriented.


Daniel Scrivner:

And examples of that are, someone says they're building a business they want to have it for 10 years, two years later, they are out of it or they flip it or they sell it. It's not necessarily a good or bad question, but I do think there's something I pride myself on being long-term oriented. I really tried to do that. It's important to me for a number of reasons. So I would just love to dig in, why is that so important to you? And was there a defining moment, a defining story, a defining figure in your life that helped plant that there?


Ryan Boykin:

I'm not sure if there was a defining figure in my life, but there have been defining moments. I think that sometimes people talk about being long term and then they end up being shorter term. A lot of money is dangled in front of them in many of those instances. And you've just been through this champions walk of fire for five or 10 years of building a business. And for anybody that hasn't built a business before, hopefully they can hear this and they can hear it's really damn difficult. And for anybody that has built it, I think they would corroborate, it was way harder than they thought it was.


Ryan Boykin:

So you get tired. You just get to a point where you're like, "Wow, this is a culmination event." And then your mind gravitates to some of these short-term pleasures. It would be great if I was sitting on the beach and Nicaragua with my wife and drinking a squishy drink and surfing every day, that's where your mind gravitates towards, and as it should, because that's the dopamine, it's all the great things that we feel when we get to have that relaxing moment.


Ryan Boykin:

And I've had those moments where I said, "Wow, I can take a deep breath here." I think what's fascinating is that when I've had those moments, I've realized that it's been really fun to get away and have the monetization moments and get away from everything and just relax. But that as I study myself, this is a self-reflection point, as I study myself while I'll have the fun of doing that little thing right now and the getaway, it isn't the fulfillment. For me, I am fulfilled as a human through an incredibly purposeful mission-driven existence, by serving other people.


Ryan Boykin:

And this is my modicum, this is my vehicle. I'm not smart enough for my vehicle to be through science or through politics or any that kind of stuff, I'm only smart enough to do it through business. If this is my vehicle, then I want to capture it. And a lot of times, even today, I say, "Why am I subjecting myself to this fire again? This is so hard." And the reason is, because I crave the fulfillment, and that fulfillment comes over the very long term. And it's even more fulfilling for me when I realize that it doesn't have an end point. I'm not going to say that I'll never sell my business or businesses, or I'll never sell my real estate or you name it.


Ryan Boykin:

That would be absolute, and I think that's making a decision in a vacuum, but I will say that my goal set is to create a great place through which humans can thrive and through which we can serve the planet in my businesses. And as long as we're doing that and we're still sustainable, meaning that we have a profit, then my great proclivity is to continue to build for the long term because it's fulfilling for me and it's fulfilling for the people it touches.


Ryan Boykin:

And I believe in the ripple effect that that can be on the world. And so that's just comes through my own self-reflection. I don't know if that holds for many other people, but I look at some people that have been on the journey for long periods of time and mentors that I've had, Steve Demos who started WhiteWave Foods and eventually sold it to Hayne. He ran it for 17 or 20 or 25 years or something like that. And he never made a buck and along the way. He finally got to the end and it made sense to get to the end, but he built something that stood the test of time and that was a beautiful business, and it was formative to me in my early days. So maybe that's a figure. That was a part of that story.


Daniel Scrivner:

Yeah. It's super interesting. Where my mind goes is thinking about infinite games versus finite games and even something like working out where I think for a lot of people, they're like, "I want a certain body, but how does working out work?" You get that body through exerting a bunch of effort. You don't keep it, you don't just walk away. It's about this discipline and the practice and enjoying and becoming a better person and doing good through that work itself, which I think is really interesting. I want to explore, you talked about wonderful quote of making sure that you don't launch a business that needs more than one miracle.


Daniel Scrivner:

I would love to try to make that a little bit more tangible and maybe there's an example as you thought about founding and launching Atlas and REACTIV, and maybe it was more conversation with someone that is getting ready to found a business. How have you taken or how would you take that advice and put it into practice? When do that something is not going to require multiple miracles? How do you try to make that tangible?


Ryan Boykin:

Tangibly, that might be a tough one. I think that when you say that starting a business and having success of the business is a miracle upon itself in and of itself, then you're already starting with one miracle, and that's even for a proven industry. The businesses that I've done, some of them have been very proven. Buying real estate and holding it, that's pretty proven. The miracle that we took on in that moment was we were buying it at a moment when everybody thought the world was over.


Ryan Boykin:

And with Atlas Real Estate, we were telling people, "Hey, we're going to be a broker, but as a broker, we're going to show you how to buy an investment property, and we're going to be a property manager. And the only thing that's different about us is we own a lot of real estate ourselves. So we will probably be better as a property manager than the other crew." But you have all this, the miracle in it is can you compete with all these other businesses out there that are amazing? A lot of times I've looked at venture capital style deals and I've said, "Those are two-miracle deals, I can't do that."


Ryan Boykin:

And sometimes it's okay, you're going to have to build the business and hire the people and sell in the market and compete with everybody else, but you also have to frankly tell somebody that you are a product even exists. I don't need to train somebody in real estate that real estate exists, they already know. So I've already won on awareness. Then the only thing that I need to train them on or sell them on is that my features and products and services are better than everybody else. I've already done 80 or 90% of the sale the day I meet them because they already know they should own real estate.


Ryan Boykin:

And so you think about some of the new businesses that are there, that are on the bleeding edge instead of the cutting edge, a lot of those are two-miracle deals because the timing associated with getting that product out to marketplace is just prohibitively difficult, or you need to have copious amounts of money to be able to hang in there until the timing is right, or you need to have copious amounts of money to be able to go broadly across a large segment to the populace, to tell people that this can exist. There's a lot of two-miracle deals out there that are some of the most valuable deals, valuable businesses our world has ever seen.


Ryan Boykin:

And I admire the people that started them, and I think that they'll continue to happen. I just tend to stay away from two-miracle deals. I think that they're too tough as one miracle deals, and I'm trying to wait the cards in my favor a little bit.


Daniel Scrivner:

I think that framing is really interesting, and I love you touched on it really briefly of seeing venture capital deals as a two-miracle deal. And my immediate thought was, "No, they're 100 miracle deals, because the deals like if you look at an outcome to obviously the bar in that industry, which you're very familiar with is coming a unicorn. And it is absolutely insane to be an investor in some of those deals because they just do not happen at all how you think they would happen. And they're very circuitous, and there's super down.


Daniel Scrivner:

There's a lot of lows and a lot of highs, and it can take a long time for them to materialize, but it's a fascinating insight because it's just really interesting. And that also obviously helps to drive the return profile and also helps drive the sense that it's a fat tail. If you're investing in 100 miracle deals, you better invest in a lot of them if you want to have even one or two of them come to fruition.


Ryan Boykin:

It's fascinating on the venture side for the common investor, if we said, what's your best risk reward outlook? The common investor isn't able to do 100 deals in the venture world. And so I just keep on raising my hand to the average Joe and saying, buy a piece of real estate, get your 10, 15% a year for 20 years and you're going to be just fine. And that's somewhere where I revert to of like, that's almost a no miracle deal. That's something very cheap bull for many people across the country. Now, there's other ways that we de-risk it, or there's other ways that we add more reward to it, primarily through who's operating that deal, AKA the property management company and the company that helps you find it.


Ryan Boykin:

And in addition to that, geography. And geography is a really big deal when it comes down to real estate because if you invest in a place that is not economically growing, then your real estate deal will not economically grow. They're directly related, and it's amazing how few people actually study that versus in a place like Denver or Boulder, where we are, or all the other markets that Atlas is in, we're sitting there saying, the cards are weighted in our favor because there's a ton of demand coming to these markets and we have constrained supply. Therefore, we're going to get rent appreciation, and we're going to get asset appreciation.


Daniel Scrivner:

Now, actually just a side commentary, but now I really want to check on Atlas because I don't have any rental property, it's something I've looked at, so no. I need to check that out coming out of this, because I've had the same thoughts and it's just extremely challenging as an individual investor to try to do market research, know that you're going to be able to figure out a property, that you're going to be able negotiate and manage it. It's a long road.


Ryan Boykin:

I'm going add one more thing to this, which is one of my greatest mentors and advisors in life is a shared friend, Sina Simantob. And about 10 or 12 years ago, he explained to me on a personal investment strategy, it was like a pyramid. And the base of that pyramid is the biggest swath, is the foundation. And that base of that pyramid was real estate for him. And then above that was maybe stocks and equities. And it wasn't until he got to the top of the pyramid that he said, that's where my venture capital stuff goes. For the common investor, a lot of times, that's the way it should look.


Ryan Boykin:

Now, if you're a professional investor and you say that you're going to be a venture capitalist, totally different thing, but on a personal finance level, it's amazing how little emphasis we put on our real estate as the foundation point for our financial survival


Daniel Scrivner:

And how few people I think as well are overly opinionated and are only invested in one type of asset class, which is a whole different thing, but I think even just the concept of understanding that there is a pyramid and you shouldn't pick and choose or decide which one you like best, you should just indiscriminary own all assets across that pyramid, is still really hard for a lot of people to grasp. It's like the barbell method. So I want to go and talk about some advice that you would have for entrepreneurs coming out of this experience.


Daniel Scrivner:

And you talked about that cold walk and how brutal it is to go about building a business. I also know that it's just as brutal to try in business and fail. No matter whether the outcome is great or whether the outcome is terrible, it is an extremely trying experience. And I'm curious one, what your advice is or what your advice would be for when you're talking with an entrepreneur and they're realizing that for the first time or they're in one of those really low point moments where things are really tough and their back is up against the wall. What would you like to have heard in those moments? What's the advice that you give?


Ryan Boykin:

I think that when you're contemplating starting a business, the first step is to actually have a very honest conversation with yourself and your spouse or people close to you about your station in life and whether or not the timing is right personally. When I started businesses, my first one I was 21 years old or something, or I don't know how I was young. And somebody said to me, "Ryan, in life, you're going to have three things. You got family, you got work, and you got friends. If you're going to be an entrepreneur, choose two. You're not going to be able to do all three." So I chose work and I chose family.


Ryan Boykin:

And so I confronted that, that was a personal like fact that I had to understand. When I started businesses, I was dead broke, but I didn't have any expenses. I didn't have a wife and kids, and I shared a room for 300 bucks a month, and that was the case for a long time. So I think that assessing where you are and what is required for you to be a healthy, happy human is important when deciding, I'm going to make the biggest bet of my life. And sometimes that step has overlooked, the timing step. You usually have a better chance at things younger because you have less responsibility both financially and otherwise. So that's maybe something to consider.


Ryan Boykin:

Then the second thing that I would think about is we don't do a good job of training people that it's okay to fail. And the biggest thing that you're going to lose if you start a business, by far the biggest thing is your time. And then you ask yourself, "Okay, I lost that time." And really it's about shifting your mental mind frame to go from I lost that time to I got an amazing experience or challenge that shaped me as a human. And for me, that's always been my metric. Will this build character? Will this be something that will make me a more dynamic, whole human, whole humanity?


Ryan Boykin:

It was easy for me to confront that and see the expense of my failure, because to me it didn't feel like an expense, I was going to continue on my journey and the character building of being a person, but for many, the thought of failure and the actual failure is devastating. And it speaks back to before you begin that journey, understanding where you are personally, so that you can cope with those difficult moments. And the stress that I inflicted on my body during a 13-year period in the beginning of building this, was totally unhealthy, I'm sure, yet I was thriving through it.


Ryan Boykin:

So for some crazy reason in my head, that was okay. And I think that the final thing that I'd say to that entrepreneur is take the damn risk. We are paid double, triple for the risks that we take in our life in most occasions. Assess it for sure, but even if you're not totally certain, take the risk. We need more risk takers more now than ever in my opinion. And I have been so incredibly rewarded financially and otherwise for the risks I've taken.


Daniel Scrivner:

Amen. That's incredible advice. I want to switch to the next phase of that question, which is, you talked about when you first started out, just like with anything, obviously you have no idea how to balance your ambition and staying sane. And there are plenty of people I know that it just takes you a long time. I feel like I'm still learning that, I'm in the middle of my 30s. I'm still trying to figure out how the hell to balance ambition with all the other things in life. And I know that that's something that every entrepreneur has to grapple with and can be a really tough topic. So I'm curious, how has that changed for you over time?


Daniel Scrivner:

You talked about those first 13 years you were thriving, but also probably weren't taking the best care of yourself. What do you do differently now and what would be your advice for how to balance those things?


Ryan Boykin:

I don't do anything differently. You know what, actually, I probably fit on a different spectrum than many on this or a different side of this question. I'm not a big believer in balance, and I'm sure people would cringe at me saying that. I often reflect that I'm either a zero or a one. I'm like a computer code. If I'm on, I only got one gear, it's all the way. If I'm off, it's all the way off. But what I realized actually is I can be on on all things. I consume and I'm with my family voraciously.


Ryan Boykin:

I do the same with my business. I always, every single time without fail, I am at home by six o'clock. I eat dinner with my family. I spend time with my son. I will not sacrifice that. And the converse of that is that I'm charged up to go to work. Now, I've made work fun for myself because I don't have as many fun outlets. I work with people that I love. People say not to work with friends, I've had more success working with friends than any person I've ever met. I absolutely love it. And I laugh a lot at work, and we have stress relievers all around our environment all the time for those moments.


Ryan Boykin:

But I'm like, if I love something, why would I do less of it? I also have confronted that there's just a lot of things I just say completely no to, I don't try to dip my toe in the water, I just say I can't do that. So I have a hard no button on a lot of things because I know how heavy my yes button is.


Daniel Scrivner:

I love that. The question I was trying to ask there is, so there's the whole notion of balance, but I think totally separately from that, there's realizing that you can't go all out without putting good things in. And those good things in can be time to reflect, can be time to meditate, time with friends and family, can be going into a hot sauna, can be going in cold water. And it seems like you are particularly good at that side. I guess, has that had a substantial change on your performance? And can you talk a little bit about some of the things that you do there?


Ryan Boykin:

Probably all of the above, and it's had a giant impact on my performance. Probably about four years ago, I got really serious about my diet, not so much around my body, but around my mental aptitude and eliminating rain fog and having great clarity. So it's a lot of fasting and the food that I eat. I've only been taking cold showers for probably the last four or five years. And I live on a lake where we do ice plunges every weekend in the winter. And about a year and a half, two years ago, I started meditating about an hour a day, mostly just on weekdays, actually.


Ryan Boykin:

Those things do speak to balance, and I'm very healthy in terms of physical fitness and all that. They may seem as though they're balanced. What's interesting is I'm just asking myself, what do I do that makes me feel the most invigorated and alive. And in that sense, it's all the same looking glass. The other thing on this, Daniel, is I do believe in turning off that regimen because sometimes there's like such a didactic commitment associated with those things that it can be exhausting. And if it gets to the point of exhausting, then it is no longer sustainable.


Ryan Boykin:

And I've thought about that with my companies as well. If we all work to the point of exhaustion all the time, I may be able to do that, but that's pretty unusual. We're going to get to exhaustion and then that's a breaking point. So my personal life on those items, on the weekends, I let myself do what I want. I'm going to sleep in a little bit, and I don't meditate on the weekends too much. We meditate as a family every week, but that's a short meditation in comparison to a one hour. And I eat, and I drink alcohol, and I play, and love to dance and party and all those things.


Ryan Boykin:

And so that really enables some of that stress relief and some of the checking the fun box. And so that's been a nice cadence for me, a regimen during the week and peak performance, and then on the weekend, I get to goof off a little.


Daniel Scrivner:

Spend time with family, recover, recuperate. We're going to go a lot deeper into what we were just covering in the next bonus side of this interview. So to wrap up this one, we've covered a ton of ground, and to be super frank, I feel like I've got another hour of questions, but we'll leave this one here. We can maybe come back and do another one. So just to ask one closing question, for anyone listening, the people on this podcast are entrepreneurs. They founded business, they're building a business right now, they're in that pursuit, they're in that arena. What final piece of advice, final piece of wisdom, final words, would you leave everyone with?


Ryan Boykin:

I'm going to give two little things. One, we didn't touch on, and I think it's important touch on it, REACTIV, which is my newer business is a venture capital PropTech-style business. And in that respect, weighting risk and reward, I think it's important just to comment on this. The moment that we're in and building a venture capital backed business, the risk is just as high as it's always been. It is very likely that I'll be unsuccessful in this business. That's what the percentages say. However, in the moment that we're in, we've never been so well rewarded if we're able to pull off that giant miracle.


Ryan Boykin:

And so in the same way, I'm still assessing risk and reward. It's just that I'm putting more emphasis on the reward side. The risk is about the same as it's always been, zero. The risk can't get much lower than zero, but the reward side is what tempers that. And so in this moment, the risk reward assessment just looks a little bit different. And the advice that I would give to somebody embarking on their entrepreneurial journey, more than anything else is to do it. I've just been so rewarded in my life through this, even through the failures and the difficult moments.


Ryan Boykin:

Nike got it right I guess when they said just do it, although I wish I could come up with something more inspirational, although, hey, if you've never read the book by Phil Knight, Shoe Dog, there's an entrepreneur's journey. So in that regard, that is a fun book that speaks to an entrepreneur's journey.


Daniel Scrivner:

It's a fantastic place to end it. It's all about the journey. Thank you so much, Ryan. This has been a great conversation.


Ryan Boykin:

Rock on, Daniel. I've really enjoyed it. I didn't get to ask you one question. So next time, I get to pepper you with like 10.


Daniel Scrivner:

Deal.


Ryan Boykin:

All right, buddy.


Bonus Ryan’s Habits, Influences, and Life Lessons – Ryan Boykin of REACTIV – Outlier Academy

Daniel Scrivner:

Okay. We're back with Ryan Boykin to dig into a bunch of fascinating stuff, habits, tools, routines, influences. Thank you so much for your time, Ryan. I'm really looking forward to this.


Ryan Boykin:

Rock on.


Daniel Scrivner:

We always start with the same question. And we talked about it a little bit at the end of your last interview, just in terms of the things that you do to put into yourself so that you can perform at the highest level. So I'll ask a slightly different question, which is, when you're, just take a weekday, since I know your routine varies during the week and on the weekend, take a weekday, talk us through some of the things that you'll do on a weekday. And some of them can be negotiable non-negotiables, but what are some of the things that you're doing in terms of habits and routines that really set you up for success?


Ryan Boykin:

Okay, that's a good one. Typical weekday, I'm up pretty early, and absolute non-negotiable is I head to our attic. We have a building that's located close to downtown by the aquarium in downtown Denver for those of you that happen to know this region. It's an old Victorian building, and it was one of my first forays and understanding the value of unused, unoptimized space. This beautiful 14-foot high ceiling attic, it was full of cobwebs and rafters. And few years ago, we started a company inside of it called Archipelago Clubs. And we outfitted it into being a Bahamian hangout spot. And we host maybe 25 or 30 programs a month up there for people to gather in a small communal fashion.


Ryan Boykin:

Well, it turns out at 6:00 AM every morning, there's nobody there except for me, and it's such a sacred place. And it's interesting to invest in this space and moving a place from a place to a space and giving it heart. And it's funny, a lot of times I'll wake up in the morning, and I just have to race there to go sit down and to really develop my relationship with myself and with spirit, my body. And so that's a definite non-negotiable, it's something I just picked up over the last couple of years. And it came from a very difficult moment I had with my health, and it was something that completely healed me from a physical standpoint. And just so grateful for that.


Ryan Boykin:

Other things that I do on a daily basis, I fast daily, I do time restricted because I find that my mental processing speed is so much faster when I'm not eating, and when my body's operating off of fat versus sugar. I think that the quote that I read is that we digest for four to six hours after having eaten. And all of that is energy that I would like to play somewhere else. I used to be completely addicted by food. I was governed by it. And so one of the big things that happened to me over the last several years of this is I got to a place where my relationship with food became healthy.


Ryan Boykin:

I'm very food motivated, I love delicious food, but to be at a place where I can say, "I'm going to choose to do something versus my stomach and my metabolism," because I have such a raging metabolism, which is a great problem to have, but still something I had to resolve. So I'm very strict on my diet and my fasting during the week. Every day I do at least 200 pushups because I never have time for exercise. And so between phone calls, I'll just knock out 50 or 100. So a couple of hundred a day.


Ryan Boykin:

Every day I kiss my wife, every day I play with my kid, every day I'm at the dinner table with genuinely engaging with them. And I turn off my phone and my computer all the time. There's tons of times that you won't get back to me on text message and all that kind of stuff. And those are probably the non-negotiables. And of course, I work a lot. Sometimes I get worn down at looking at my computer and my screen. I don't see those as personally fun devices, I see them as work devices. And so people that want to interact with me on those devices, that's a real challenging one for me. I'm just I'm really slow.


Ryan Boykin:

And sometimes I lament that because that's the best way to keep in touch with people overseas, and I have deep relationships overseas, but that's one of my Achilles heels.


Daniel Scrivner:

That's probably one of the best, most comprehensive answers I've gotten to that question. So that's great. I want to ask just a little bit more of what you do in the morning, and I'm curious if there are specific practices that you do, those could be journaling, those could be sitting down. What helps you get oriented or what's the process use or the tools you use to get to know yourself better?


Ryan Boykin:

Yeah. I think my favorite way to start the morning actually is to ride my bike to the office, and I get a little bit of the physical in. I'm very physically oriented. I find that I'm better when I physically exert, but usually, I'm riding my bike to this attic spot if I'm doing that. And I can't do that every day of the week. And then I get there and typically I'm going to sit down and it's usually a guided meditation. That's going to get me into a head space that is very strong and enables me to work on me instead of work in me in the same corollary that you need to work on your business sometimes instead of just in your business.


Ryan Boykin:

And generally because of the practice and having given myself an hour, which was unfathomable for me when I began this practice a couple of years ago, I never thought I could sit for an hour, but when you go that deep, then when you come out of that, you're more in tuned to assess some of the more profound components of your life. And so I almost never can go directly into work. Actually I have to take time to get to a point where I could even think about working and checking email. And so I don't journal every day, I journal when I have something on my mind that I need to frankly have therapy with.


Ryan Boykin:

My journal is a therapeutic device first and foremost, I've noticed. Secondarily, it's a device through which I solve problems and helps me to think through very complex issues I'm working with internally or externally. And then I'd say tertiary, a third for my journal, it's oftentimes an epiphany that I might have or something that happened that somebody said and I said, "Geez, I just need to go deeper on that topic to understand what it means to me." And I guess from a final perspective, sometimes I just want to remember a day, and it actually turns into a diary.


Ryan Boykin:

And I had an experience that I say, "This is an experience I want to share with my son one day." And maybe my journalist turned into something where he might glean one aspect of what the day in the life of his dad was in the early 2000s. My grandfather was born in the early 1900s and he passed on to us a memoir when he passed away. And I remember reading it when I was 18 years old and it was meaningful to understand the human experience and understand the plight of how we have run over 100-year period and how much progress we've actually made.


Ryan Boykin:

That is a statement to the positivity through which we actually live in. And you have to see that from stepping back, that long term we talked about, the forest, the trees, you can't see it when you're on the micro. And then from journaling, usually some stretching and some pushups. And then I usually go to the bathroom and then I can usually start my day in terms of work.


Daniel Scrivner:

The most important part, the bathroom break. I want to talk a little bit about leaving something, using the journal to one, I love that concept of there was an idea or a quote or something somebody said and you want to go deeper on that. And I also love that note that you said of noting things that you want to do with your son and just having something written down that you can pass on. And the one thing I'm going to share is my wife, who is a much better person than I am in almost every way, she's an amazing person, but she started a practice with both of our sons where every single year on their birthday, she writes them a letter and puts it into an envelope.


Daniel Scrivner:

And I am just getting started with that. I'm far behind her by a couple of years, but something like that practice would have been so profound for me because I feel like just to have that dialogue, to be able to open those back up, like what more meaningful thing can you pass on? This seems pretty incredible.


Ryan Boykin:

That's a good one. I'm writing it down my man.


Daniel Scrivner:

It's a good one. Write that down in your journal, you can work on that tomorrow. So going on to tools, and all of these questions, these may or may not be things that you use, but there are interesting ways to explore. And so with tools, I know that you want to use your body a lot, you need to use the computer a lot, you don't necessarily like. Those devices, they're not fun devices, but are there physical or digital tools that you use? You can take this question any direction that you want, but are there things that you just have had a profound connection with or like favorite purchases, favorite things, or things that you use that you found over time and just really rely on?


Ryan Boykin:

I'm a pretty simple guy. I even think a minimalist style lifestyle would be really fun for me. That's not my world, not even close. Someday, someday maybe. The greatest tool that I have is probably my computer because I can do so much with it, but I can't take a phone call ever if I have to hold the phone to my head. So I must have some earpiece through which to talk. I just simply cannot do it. I do use tech a lot, but I'm not addicted to it in the sexy way I want to use it for the tool that it is, and I want it to work pretty well. So I'm probably going to fall flat on this one a little bit. I'm a little bit in the analog tool world.


Ryan Boykin:

And I think that the reason why I am is because I actually get exhausted with the digital tool and tech tool world. And I find that when I invest into it more deeply, I actually get a little bit more reactionary, a little bit more herky-jerky, a little bit more like look at this shiny thing as opposed to my greatest decisions and the greatest operation and execution that we do in our businesses, is in those moments that I say, "I stopped and I thought, and I perceive this to be the most accurate direction, and now I work towards that." There's a little different cadence there to how we would guide our lives, I think.


Daniel Scrivner:

That's great. I asked you this question before and you had a fantastic answer, so I'm very excited to ask it again, which is, what are your super powers? And you can take this, I think it would be interesting to maybe explore it as an entrepreneur, as an investor, and maybe as a human, but how would you answer that question? How do you think about that?


Ryan Boykin:

First thing I'd say is that there's no chance I have a superpower. It's a very becoming and complimentary question. So thank you for that, but I just really feel like I'm just a guy. I do think I work really hard. That is a super power in and of itself. A lot of people don't embrace or don't have the natural disposition towards hard work. I have that naturally. I'm really grateful for that. I do think I'm quite strong in assessing risk and reward. And all the other thing that I think about sometimes Daniel is, we don't put enough emphasis on emotional intelligence, on EQ.


Ryan Boykin:

And I don't think I'm particularly strong on this. I know I wasn't when I was younger, I really was abrasive many times, but I do think that it's really quite possible, and I don't think that our society recognizes it. It's possible to be super human with your EQ, and those that I've met in my life that are super human with their EQ, oftentimes don't get the credit that they deserve. The lubricants that they are to a community, to society, to individual interaction, the gravity through which they pull people closer to them when people don't even realize that's why they're being pulled closer to them, I think that there's a superpower there.


Ryan Boykin:

I don't know. I don't think that I have it, but I've seen it before, and I always try to aspire to learn more. And we're in a society that we say, "Oh, this person's a genius." And genius speaks to IQ, which is equally important, but I think that when we're governed by eight billion people trying to figure out how to make sense of this place, the EQ is more important.


Daniel Scrivner:

I couldn't agree more. If we're going to come together as billions of people around the planet with a bunch of different beliefs, with a bunch of different values, EQ is going to be the only way over time. On the flip side of that question, what do you struggle with personally, professionally? And how have you worked on those things over time?


Ryan Boykin:

I do struggle with saying no still. I said I have a hard no button, but I do realize that if I say yes, I am such a mad man, I'm fulfilling my commitment, that it actually can be a little bit psychologically detrimental. And that I have to be a little bit better at saying no to things, and I don't want to go so far that health is in jeopardy in terms of how deeply I try to fulfill that commitment. So I do think that I struggle with that a bit. I think that sometimes I struggle with expecting that people around me... I expect a lot.


Ryan Boykin:

I think it's unreasonable at times what I expect and I've gotten better at understanding that, but I would be a lot stronger if I tempered that a bit.


Daniel Scrivner:

Are there any people, these can be modern, can be historical figures, can just be people in your life, and you mentioned a couple in the last interview, that have had a profound impact on you? And can you share a story, an insight, something you've learned from one of them.


Ryan Boykin:

First and foremost it will always be my mother and father. I am the luckiest man alive for the family I was brought up in. We talk about where we're lucky, and I often think to myself, the old proverb or adage of, too much was given, much is required. I feel a sense of responsibility through what I had in my upbringing with my family. But to speak specifically about an experience or a person, one person that comes to mind is Dan Freelander, and he's passed away since this happened, but he was the first person that ever said to me that he believed that I could run a billion-dollar business.


Ryan Boykin:

And I was very young at the time. And it occurs to me how incredibly important it is, particularly when you're young, but I think at all stages in your life that somebody believes in you. I was an overconfident arrogant jerk when I was a kid, and yet still I was insecure. And probably that overconfidence and arrogance came from some insecurity, but to hear somebody that was wiser than me, that had been through it to say that he believed in me, and many others have said it as well, but that was something that has never left my mind. And it was very, very meaningful in the difficult moments, as well as the successful ones.


Ryan Boykin:

I could go on and on about Sina Simantob as well. That guy has been an absolute champion in my life.


Daniel Scrivner:

It's incredible. I love that example that you gave. Do you have any favorite books? These can be books, articles, anything that you either try to go back to again and again, because it just really speaks with you or anything that at some point in your life had a profound impact on you?


Ryan Boykin:

Most recently, the one that's had probably the most profound impact has been Power vs. Force by David Hawkins. And I've just absolutely love that one. I also really appreciated You Are the Placebo Effect by Joe Dispenza. I read that fairly recently. Has been a lot of great books, but I'm not strong enough to call myself an avid leader. I do also love Good to Great. So there's a few. I also love Atlas Shrugged. It's very binary, very black and white, but there's this component of being an entrepreneur where you say, "I've got to stand on my own. I got to do this. I don't get to rely on anybody else." It's sort of, I'm in the wind getting pushed and I got to go. And I think that it spoke to me at a very early age.


Daniel Scrivner:

We'll link to all those in the show notes. I've not heard of Power vs. Force, or You Are the Placebo Effect. So I'm excited to tail with us.


Ryan Boykin:

Power vs. Force is mind blowing, and You Are the Placebo Effect was the beginning point of healing my body.


Daniel Scrivner:

Wow. It's amazing. We always ask the same two closing questions, and these are two of my favorite questions to ask. Can you share a favorite failure? And I think really what we're looking for when we ask that question is, so many times in our lives, we look at outcomes as super binary, and there are, especially in hindsight and reflection so many times., and you talked about earlier, failing in a business that that's absolutely not a failure. So is there in your life a favorite failure? It can be any sort, any variety.


Ryan Boykin:

Daniel, all my failures, I've appreciated. Some of them were really, really painful. Once I had a guy that was a partner on a deal and he through the construction process, changed the name very slightly to the general contractor that I was paying the bills to. And it turns out that this guy that was my partner, that was my operator on the ground, he set up a new company that looked like the general contractor. And so every time I sent the check, he was cashing that check himself and giving the general contractor a smaller amount.


Ryan Boykin:

And over a period of two or three years, he probably stole half a million to a million dollars from me. And that was really painful. The greatest way that it was most painful was I felt like this was somebody that I knew, that I trusted, that was a friend, and I found out that wasn't the case and it was devastating to my heart. The second greatest way is that it wasn't just my money, I had investors on it as well. And I had to confront with a very difficult conversation what had happened with that money to those investors. And the flip side of it is that we still made money on the deal.


Ryan Boykin:

So it took us a lot longer and it caused me a lot of heartache and legal and all this kind of stuff, not things I want to participate in, but that's one that I think when you're in the dumps, it's good to remember, you can still crawl your way out. I had to work a lot harder, but you can still crawl your way out.


Daniel Scrivner:

On that first one, I can only imagine just someone embezzling from you, especially over a course of years when they're your partner, how heart-wrenching that is. And I have a friend in my life that has a quote that he says all the time, and it's really interesting. It's a really short question, it's seems not profound, but this also has a lot of profound levels to it, which is, try to make sure at each point in your life that you're not learning the wrong lesson. And I imagine there's a lot of ways you can learn the wrong lesson from that situation.


Daniel Scrivner:

One could be, I'm never going to trust anyone again, I'm never going to have a partner, I'm going to verify everybody, I'm going to constantly be monitoring. What did you take away from that? And how did you make sure you didn't learn the wrong lesson from an experience like that?


Ryan Boykin:

There's a lot of places I could take this question, and I'm going to take it just to one little corner. I could have left that and decided that I was going to micromanage the hell out of every relationship I ever had. And it would have been really logical to go that direction. And instead I said, "I'm going to structure deals wherein our interests are completely aligned such that we are going to win together. And in doing that, I know that I'll achieve their individual goal as well as our collective goal together." And so I've driven even further from a management solution to an accountability, a goal setting and aligned solution.


Ryan Boykin:

I had that already going for me, and this guy that took money from me, as a result, he lost his share and the upside of that endeavor. And when it turned out that we sold the deal, he actually lost more than he gained, because of how much share he lost. But that was a big moment for me to realize that alignment is everything. And particularly in this digital world that we have, if you're an entrepreneur, you want to try to micromanage your people right now, good luck, good luck. You better get them mission-driven, you better get them accountable to whatever their goal is.


Ryan Boykin:

And if they work two times faster or four times faster than anybody else, and they're doing some other things on the side, that's the reality that we're in. You're not going to be able to track it, but you can track their results, and don't penalize them for having great results just because you're not sure how much they're working, they should have upside on their ability just as you do.


Daniel Scrivner:

Ton of wisdom in that answer. And final question, I think you're going to have a great answer to this one. What is your definition of success?


Ryan Boykin:

Well, I don't think success is an end point. People say, "I'll have been successful when this happens." No, I want success to be ongoing every day, I want it to be the journey. And so as I sit back and I reflect and I look at what I've done, even when I was dead broke or I wasn't married yet or whatever, I was successful, because that was part of my journey. It was fulfilling. So yeah, my definition of success is fulfillment. My definition of fulfillment comes back to where I'm motivated as a human.


Ryan Boykin:

That means I'm solving a problem, and it means that I have the richest, most deep, beautiful relationships that I could ever possibly imagine with my parents, with my son, with my wife, with the four or five brothers and sisters in my life that I get to call true, true brothers and sisters. And frankly, with the people that touch the little bit of my world, that is my businesses and my other endeavors, for me, that's what's fulfilling, solving those problems and the meaningful relationships. And if I have that, I'll have success. I know, and I've always felt that the money would follow and I need to follow passion first, those are my passions. So that's the best I can do.


Daniel Scrivner:

Fantastic answers, fantastic interview. Thank you so much for the extra time, Ryan. This has been great.


Ryan Boykin:

All right. One question for you. What's your favorite nickname, Daniel? What's your favorite nickname?


Daniel Scrivner:

The nickname that still sticks with me, I don't know if I'd call it my favorite, but definitely the most memorable is all growing up, my last name is Brutal. Literally when I tell people how to spell it, the thing that helps the most is if I just say, it's a harsh German name. So just like, don't try to finesse it, it's just like S-C-R-I-V-N. And people push it all my life. And so growing up, people would call me Scribbles. And if I could carry that forward, I think that would be a pretty good nickname.


Ryan Boykin:

All right, Scribbles, you're the man. It's going to be saved in my phone as Scribbles.


Daniel Scrivner:

Thanks, Ryan.


Ryan Boykin:

All right.




On Outlier Academy, Daniel Scrivner explores the tactics, routines, and habits of world-class performers working at the edge—in business, investing, entertainment, and more. In each episode, he decodes what they've mastered and what they've learned along the way. Start learning from the world’s best today. 

Explore all episodes of Outlier Academy, be the first to hear about new episodes, and subscribe on your favorite podcast platform.

Daniel Scrivner and Mighty Publishing LLC own the copyright in and to all content in and transcripts of the Outlier Academy podcast, with all rights reserved, including Daniel’s right of publicity.

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