BIO: Thomas J. Powell, founder of The Powell Perspective™, is a seasoned entrepreneur, investor, and advocate for founders, bringing clarity, strategy, and resilience to leaders building at scale.
STORY: Thomas invested $3.6M in a friend’s cannabis company, where he ignored his own due diligence framework. Because he skipped key governance protections and didn’t document alignment or exit terms, the investment became frustrating, hard to control, and nearly impossible to fix—proving that breaking your own rules is the most expensive mistake.
LEARNING: Never mix friendship and business. Make sure both you and the founder are solving the same problem.
“They say good fences make good neighbors, good documents keep good friendships.”
Thomas Powell
Imagine navigating the high-stakes world of capital, strategy, and legacy with a guide who has raised billions and structured ventures worldwide. Thomas J. Powell, founder of The Powell Perspective™, is a seasoned entrepreneur, investor, and advocate for founders, bringing clarity, strategy, and resilience to leaders building at scale.
You’ve probably heard the saying, “Never mix friendship and business.” Thomas learned that lesson the hard way.
His story starts with good intentions. When his kids’ grandmother battled breast cancer, cannabis was the only thing that eased her treatment side effects. So when medical marijuana became legal in a few US states, investing in the cannabis industry felt like the right thing to do.
But here’s where things went wrong.
A close friend brought him the deal, and because of that personal connection, Thomas skipped many of the due diligence steps he usually followed through his family office. No detailed governance clauses. No proper reporting framework. No accountability structure.
It wasn’t a small investment either—about $3.6 million. As time went on, the cracks began to show. The company missed financial reports, accounting systems were weak, and when COVID hit, things only got messier. To make matters worse, taking over the business wasn’t even an option since he didn’t have a cannabis license. The emotional toll of this situation was significant, as Thomas had to face the reality of his investment failing due to trusting a friend blindly.
The worst part? Having to look a friend in the eye, knowing he’d broken his own investment rules.
Align the capital and exit terms from day one—and write them down, even on a napkin. You don’t need a 30-page legal contract to start. Even a handwritten summary that defines the key terms, goals, and triggers for selling or exiting can prevent misunderstandings later. Because once the ink dries, or worse, once the money’s wired, it’s too late to wish you’d had that conversation.
Thomas recommends these books, principles, and resources for smarter investing.
Thomas’s goal for the next 12 months is to expand his Founders Office cohort program, connecting entrepreneurs and investors to create better capital alignment. He’s passionate about free enterprise and founder advocacy, believing that capitalism—done right—can lift people out of poverty and fuel innovation worldwide. Whether in the US, Europe, or Sub-Saharan Africa, his mission is the same: empower founders and investors to build lasting, ethical wealth together.
“Learn from other people’s experiences. When you see someone make a mistake, don’t repeat it because we don’t learn from the wins, we learn from the failures.”
Thomas Powell
[spp-transcript]
Andrew Stotz:
Matt, Hello, fellow risk takers, and welcome to my worst investment ever. Stories of loss. To keep you winning in our community, we know that to win in investing, you must take risk, but to win big, you've got to reduce it. Ladies and gentlemen, I'm on a mission to help 1 million people reduce risk in their lives, and I want to thank you for joining that mission today, fellow risk takers, this is your worst podcast host, Andrew Stotz from a Stotz Academy, and I'm here with featured guest, Dr Thomas Powell. Thomas, are you ready to join the mission?
Dr. Thomas Powell:
Absolutely, Andrew, this is gonna be fun. Yeah. So
Andrew Stotz:
let me introduce you to the audience. Imagine navigating the high stakes world of capital, strategy and legacy with a guide who has raised billions in structured ventures worldwide. Dr Thomas J Powell, founder of the Powell perspective, is a seasoned entrepreneur, investor and advocate for founders, bringing clarity, strategy and resilience to leaders building at scale. Thomas, take a minute and tell us about the unique value you are bringing to this wonderful world.
Dr. Thomas Powell:
You know, Andrew in my career, of which started my first company over 40 years ago, but started investing strategically in companies starting in 92 so it's been, you know, 3334 years now. And so what we bring is a unique founder advocacy and oftentimes our CO investors in deals are also founders that have had exits. So we align capital with clarity, governance and integrity.
Andrew Stotz:
And as a founder, I mean, how do founders find you? Where is the place that they you know? Where do they find you? Online?
Dr. Thomas Powell:
It's been an interesting story, because, for the most part, people could only find us by introduction. I didn't have a big web presence or anything out there. We that was actually part of our underwriting of both our investors and the deals that we looked at was Who introduced you to us, and kind of the best known secret out of Silicon Valley. Now we actually do have a website. So our family office, which is called the Brahan group, led a venture now called the founders office. So it's founders dash office, horrible moniker, but founders dash office.com and that's where you find all of the services that we provide to both founders and founder investors, which is groups that we service on this,
Andrew Stotz:
and how wide or narrow are your services?
Dr. Thomas Powell:
Generally, they're the early stage capital raising. So generally, if a company's 10 million US revenue stream to about 100 million US revenue stream, and they're looking to scale, and they're bringing in that next stage of capital. So they're way beyond, you know, friends and family, but they aren't necessarily looking to do a round. It could be structuring the institutional capital. We could be using unique finance products that we've done worldwide through one of our arms that's very bespoke, so we can do larger deals as well. But we really love those founders that are in that range, they've got an idea. They've proven that they've got a market and they're able to grow it. They just don't realize that bringing in capital is a full time job, and as investors, it's oftentimes they've exited a company. They've got, you know, 1015, 20, 100 million more than that, sometimes, and they want to go invest, but typically they're finding the investments were which were them, so they're identifying the founders, that was just them, and they don't have any framework of what to do. So they end up either losing a lot of time or a lot of money, or both, because they don't have a specific investment and they're just bored of doing institutional investment. So, you know, they're like, that doesn't fit me really well. I want to have more control. So those are the two groups that we really service
Andrew Stotz:
and what is the investor looking for at that stage. So you've got, actually, you've got a few different stakeholders. You've got some original, let's say angel investors and others. And some of them may say, Well, I've had enough of this ride. Can I somehow figure out a way to get out? And others say, No, I want to continue this. But that's on the original investor side. Now you've got new investors coming in. Are these new investors saying, I want to, you know, be with this company for life, or I want to do help them get to the next or I want to help them list, or I want to help them what? Or I don't want to help them. I just want to put money in and get a return. How does it look there?
Dr. Thomas Powell:
It's all across the board, Andrew, because sometimes it is the and the the easiest, but also the worst investor is the one that's I just want to return, right? And I'm going to get in and get out, and that's generally where we in a capital alignment model. What we do with the founders and with the investors on both sides, we get them to match what's the problem that's being solved. So one of the books you've got all your books on the background, the richest man in Babylon, is one of the books that I just absolutely love. And it's because it's so simple. It says, invest in something you know and understand, and then invest with people that know and understand what it is they're doing. So we use the scenario of, do you understand the problem that's being solved, and if you understand the problem that's being solved. And then the solution is relatively simple, even if it's complex, but it can be described that probably will be a decent investment. And somewhere down the line there's going to be some liquidity event so you can get back out.
Andrew Stotz:
And, you know, I'm just curious about it, because it's some there's two things I was thinking about. You know, some may say to the investor, the investor, or, sorry, not the investor, the founder may go, oh, I can do this myself. As you said, you know. And, and that's, that's one thing. And then what, what I was also thinking about is, like, what, what is a what should a founder expect at this point, you know, they're at this level. They're talking to these types of people, you know? So maybe you could just address those two things. I'd be curious to hear what you'd say.
Dr. Thomas Powell:
So the founder oftentimes will think, you know, they've had some they've had a lot of success, in many cases, especially if they've grown a company to $10 million throwing off cash. They're usually living a lifestyle. They've moved into a space that we named partial academics. So of course, we have to name things. So we've named this the founders isolation paradox, which is where the founders grown the company to the point that they have these advisors, usually their C suite of people. They have these outside counsel, outside accountants. Their spouse probably helped them start the company, and none of the and their banker and none of those people in their sphere are actually aligned. So at 2am the founder is sitting there looking up at the ceiling, still trying to make decisions all on the decisions all on their own, because none of them have all of that. So that founder that's gotten to that point also has had a lot of success, because a lot of times they deem themselves the smartest person in the room. They've been able to get it going by grit. They've been able to figure out what regulatory problem, whatever it is. But they come up to this barrier, which is now capital starts becoming more sophisticated in most cases, and so and it needs to. And it's larger dollar amounts. It's not just your mom lending you her credit card to start the company, right? So it's like, how do you grow this and how do you align it so that it actually matches the goals of the company in the short term and in the long term? And does it match the executive team? Does it match the founders? Where do you have to look at that caps, that cap table, and all those pieces come in and and if you go talk to a lawyer, in most cases, they're going to know some of that, but they haven't even actually ever done all those processes themselves. That's part of where we come in, and we're actually the founders advocate. And to take a back story, and in 92 as I'm coming out of Silicon Valley in the 80s, working for a large bank, we were seeing more and more founders being kicked out of the companies by the money. And having been an early stage founder myself, I'm like, Okay, how do we help coach these founders where they're never generally going to grow into being a professional CEO, but they can find the right way to lead and guide a team and grow that company and get a good exit. And that's been our story since 92 interesting.
Andrew Stotz:
I own a business that's about at the revenue level that you talk about, and with my best friend Dale, who's been running it, coffee works. It's called for, you know, we've been running it for 30 years. In fact, tomorrow I'll sit down and it's the 10th tomorrow, and we'll review the financial statements of the prior month, and we close the books on a monthly basis for 30 years. So we have that part in good shape, but, you know, it's gonna it's interesting to talk to you about it, because it makes me think, yeah, you know, there's a next there's another stage of growth that requires first capital, but probably also new thinking. And I think every business ultimately ends up being a one man show. It's just a question of, how long can it survive as a one man show? And if you want to expand your business to be 100 million in revenue, you can't do that as a one man show. And so, yeah, yeah, fascinating. I appreciate you sharing your experience on that. So I think for the listeners and the viewers out there, make sure to check out the website. I'll have links in the show notes so you can, you can get there. But now it's time to share your worst investment ever. And since no one goes into their worst investment thinking it will be, tell us a bit about the circumstance and leading up to it, and then tell us
Dr. Thomas Powell:
your story. So it was a fun time. We were just in the midst of actually coming off. So my daughter, who, again, runs our family office, she's like, Oh, Dad, Yeah, Dad, you have to talk about the, there's a, there's a podcast out there where I'm talking to Joe Polish, and it's where, you know, we I lost $400 million so of course, that would be the one we should lead with. But that's not the one that's not the one that's caused me a lot of my aggravation of, why did we do this? And so we have an investment in cannabis. And the backstory on that, whether you're pro or against cannabis, the backstory was my kid's grandmother had gotten breast cancer, and the only thing that really worked with that whole treatment pattern was cannabis, and cannabis was just becoming legal in a couple of states for medical marijuana. And we're like, need to help this get done, because this does really seem so let's invest in this. So I had a lot of other things going on. I had a friend, which is problem number one, because. Then we bypass some of the checks and balances that we always use for investments, right? The friend bring me the deal, and then I turned it over to my team and said, put this together, and we structured it in a really brilliant way for them to be able to grow their company, but in doing the documents, they didn't put some of the typical governance pieces in there. And so it's not, it's not a huge investment for us. It's about $3.6 million it's not a small investment, but it's not, you know, it's just an irritating investment because it's a friend that I got to look across the table with all the time. And so part of the challenge was, as it went on, and I started taking more time and looking at it, I start bringing in the governance pieces. And I'm like, Well, if we haven't caused these governance pieces, the, you know, binding pieces that we look at with this to be done in the covenants, how can we go ask now, because
Andrew Stotz:
three, four, what does governance pieces mean? Rough. I mean with, I'm not asking you to give out secret details, but just what does governance pieces mean for someone that may not understand that term?
Dr. Thomas Powell:
So it's in our documents. We put how often they were going to report that they provide the general ledger to us so we could do an external audit on their auditors that they would actually use true gap financial, you know, financing regulations, which is hard because cannabis is not regulated under gap, right? It doesn't have federal but it was very important to say, Okay, we still need to meet this for our own investment strategy. So we call those
Andrew Stotz:
accounting for agriculture is really difficult, particularly intellectual property related to breeding and genetics. It's incredibly complex,
Dr. Thomas Powell:
all of that, all of it, right? And then we go through covid As part of this, right? So all of these scenarios are within there, but we do have the governance in our documents. So again, they're items that say, Hey, they need to at the end of the quarter, they need to provide financials to us. Well, no one checkboxing that, because it's one of Tom's personal investments. Then what ends up happening is all the systems and frameworks we put up around everything else, and 3.625 is a big enough investment that it pisses me off. So it's like, now I'm wasting time and money getting back in there and steering the ship, and then we get into the second part of this is you need to have people that are licensed, and I have no desire to get a cannabis license, right? So if we take over the company, we're at a scenario of where do we actually have to find next cannabis person? Which gives you a small market, which, when you only have a small exit market, you lower your prospects of how you're going to exit. It's how to have the leverage of driving this. And again, we did this as a shared appreciation loan, so it wasn't a pure equity deal, but normally we take a seat on the board. We made so many errors, and the main one was Andrew. We didn't follow our framework. We have a framework, and because it was a friend friend, we stepped outside of that framework. And then the checks and balances that we have, we didn't feel comfortable doing that again. So the overall arching thing is we never lend to friends, right? That's a narrow unless it's the same by, you know, they say Good fences, make good neighbors, good documents, keep good friendships. Yeah.
Andrew Stotz:
So what I want to do, I mean, you've said a lot of stuff there. It's a bit repetitive, but I really want to go back and have you summarize the lessons that you learned.
Dr. Thomas Powell:
123, First, verify alignment. We've talked about that earlier. We talked about that even pre show. What is it in the storytelling. What problem are you solving as the founder and as the investor? What problem are you thinking they're solving? And is there alignment in there? And is there an alignment on what the process is to get capital? Now, we can't control covid. We couldn't control, you know, 911 all these things that happen, markets happen. But if everything's going along the line, are we still aligned of what the deal is? And so one very, very simple test that we use is we use the when will you sell? And so my scenario is, if this business now was worth $25 million would they sell? And if the founders say no, and we don't have any triggers for that, I'm stuck getting carried along there. And so I tell this to, you know, I taught this to my daughter years ago. I said, every time you get an offer and you don't take it, you just bought it for that price. So somebody came in and offered us $25 million and we think it's worth 35 but would we pay 25
Andrew Stotz:
for it? So when you're saying, When will we sell? You mean, as a outside investor, when would you sell? Yep, okay, all right.
Dr. Thomas Powell:
So, so that's the verifying the alignment. The other one is really, really understanding and watching the hubris. And this is difficult in some sometimes, because we've got a large Legal Group and large. Learning group. And you know, bunch of smart people educated all over the world, from Harvard to Northeastern, north, you know, I mean just strong, strong minds. And so, know, the legal and the regulatory landscape, and we all it's, you know, it's like looking around the corner. Can you see around the corner? And who has that insight? Because somebody's been there. And then the last one is really, what are the enforcement mechanisms for accountability? So in the cases of like when we make a loan, let me say your financials are due to us on the the end of the third quarter, at the last day of the final month. And if you don't have those, you are in a default on the loan. And these are then the points that go down there and and the last one I'd say that works really well outside of the United States is arbitration outside of the United States works really well. Arbitration clauses in the United States are crap. So arbitration, for the most part, in your international they set up the rules for arbitration before you go into arbitration. You've already picked, hey, we're gonna pick one arbitrary. You're gonna pick the other one. They're gonna pick third. We're gonna arbitrate it in Spain. We're gonna use Spanish law. And you're in Thailand, and, you know, we're here in Germany, and you set up those rules for divorce before you ever do the deal in the United States, they just say you'll go to arbitration,
Andrew Stotz:
which is a whole new battle,
Dr. Thomas Powell:
wow, yeah, it's
Andrew Stotz:
interesting, because when you're operating globally, you kind of have to figure out, okay, what language, yeah, what legal structure, what legal structure, yeah, where do we want to be?
Dr. Thomas Powell:
Where do they have their assets? Because if you all of your assets are in Thailand, and we take you to court in Spain, because that's what we agreed to in Spain, but that doesn't do anything for us
Andrew Stotz:
in Thailand, yeah, yeah, interesting. So it's the same way
Dr. Thomas Powell:
in the US, because we have 55 terms. And if you know you're in Nevada, and you're in all these other areas, and all the assets are in Nevada, but you don't sue them in federal court, and you sue them in Wyoming, you can't really easily get to the assets in Nevada.
Andrew Stotz:
Yeah. So you mentioned alignment, and he talked about watching for
Dr. Thomas Powell:
single and regulatory landscape, and what triggers do you have to enforce accountability?
Andrew Stotz:
Yeah, that's great. That's great. And one of the things that I was thinking about is, you know, one of the things that I see, particularly with startups, is that they are underpaying themselves. And what, what happens there is that, as an investor, you have to make sure that they're paying themselves market price. And as I tell people, I said, when I give presentations about valuation, I always say, they ask me, how do we increase the valuation of our company? I said, double your salary. Yeah, and they're like, What? How could doubling our salary do that? Because it would put you in loss. And then you realize, holy crap, we're not paying market rates. And therefore, what's going to happen when a buyer comes in is they're going to say, okay, yep, well, we're gonna have to double all these and we have to take into consideration, you know, how would we run this if you weren't there, and you you're licensed, and we're not, and we're gonna have to figure that out. And this just reminded me of that. So for the people out there who have a startup or a business, you know, double your salary, and that's, that's a big one.
Dr. Thomas Powell:
Well, I think, you know, Andrew, I think that says something really, which we try and do in our, in our founder advocacy, is being the employee, is a job that's a salary, compensation plan for that. Being the founder, being an owner, that's a position that's different. So you and your partner go meet, and you go over the books, and if he's working in the shop all the time, he should be getting a salary for doing that. And then separately, you guys are taking out your ownership pieces in that. And if you're bringing some other value that's paid for that time versus exchange of intellect or whatever, that's one deal. And when you can segment that out, you do prepare yourself better for an exit. You also prepare yourself just for better management.
Andrew Stotz:
So let's go back in time and think about a young you know you in that situation. So let's imagine that person today is you know, their friend comes up or a deal comes up. So based on what you learned from this story and what you continue to learn, what one action would you recommend that person or our listeners to take to avoid suffering the same fate?
Dr. Thomas Powell:
Just one action, if we looked at it as the primary failure, was that we didn't align the capital and the exit well from the beginning, and it didn't get documented well. And I'm not talking about 35 pages written by the attorneys. I'm talking about back at the napkin. Here's the three points that we need to get to, and we can define those points. That is the most important part. I think it makes for a good marriage. I think it makes for a good investment.
Dr. Thomas Powell:
Great.
Andrew Stotz:
And what's a resource you'd recommend for our listeners?
Dr. Thomas Powell:
Well, I'll tell you. Well, first I would say, if you haven't read The Richest Man in Babylon, it's like, one of the simplest books out there in the world. But it's been around for, you know, a long time. I think it's 1960s is written, maybe even before that. I read it when I was pretty young, and I just love it, that it's like, invest in something, you know, don't get caught into. And we've taken. To another step. Invest in a problem. You understand that needs to be solved. So you don't have a coffee shop. And if somebody's going to do a coffee shop there, and you know that everybody's on that corner, great. You understand that. Go do the problem, the cannabis, various pieces in there. The second one is, we call it the bigger pile theory, or we call it the bigger pile theory, which is, take advice from people that have a bigger pile than you. Don't take it from people that don't have a bigger pile than you. So meaning, if so, find people that are really know it. Don't just theorize on it, but they know it. They've been there. They hopefully can see around the corner. And the third one is, we've got a pace that whether it's a founder. So let's say you and your partner want to raise capital. You can go out to our founders, dash, Office website, and you can take your pitch deck through and we'll give you a benchmark of where you're strong, where you're weak, and what you should look at, which goes through our investment framework. We also do that for investors. So if you're investing in a private company, even a public company for that matter, but you want to take their pitch deck and run it through our system, we'll tell you where we see it align in a strength and what weaknesses in that area. We don't give investment advice off of it, but we do say these are things you want
Dr. Thomas Powell:
to look at. Great, great advice.
Andrew Stotz:
Yeah, and we'll have that link in the show notes. By the way, the rich man in Babylon was written in 1926 Yeah, it was. It's an oldie. It's an oldie. It's a great part. Yeah, definitely. All right, last question, what's your number one goal for the next 12 months?
Dr. Thomas Powell:
Wow, my wife would say it's about skiing, because I ski about 100 days a year, but we actually were. We've started a founder and founder investor cohort program through the founder's office, and again, it was my family led to take the intellectual experiences I have of over 40 years and putting it down into a model where people on both sides of the transaction so we can have a capital alignment. I am a fierce free enterprise saves the world person. I'm dual citizen EU and US, and work through Asian and other, you know, South America. And I just love our founders. No matter where I go in the world, I was good place down in Tanzania, not that long ago. And we had all sub Saharan founders come to our house in Lake Tahoe, not all of them, but we had a large group come to our house in Lake Tahoe and spend a number of weeks with us. That was fascinating. So I love working with founders. I love working with the founders capital, the people that have had an exit and they're putting the money back in and aligning that capital.
Andrew Stotz:
Yeah, free free enterprise, free markets. Great stuff. In fact, I kind of it's kind of sad where it's gone. I mean, I stand up in front of people now, whenever I speak, I say, I literally stand in front of them, and I say, I'm a capitalist and profit is my passion, and they can't. They're like, Oh, my god, somebody said it.
Dr. Thomas Powell:
Yeah, no, yeah,
Dr. Thomas Powell:
I lived it. It took me out of poverty. I'm very thankful for that model, and it took us all out of poverty. Yeah? Absolutely, absolutely
Andrew Stotz:
fantastic. Well, listeners, there you have it. Another story of laws to keep you winning. Remember, I'm on a mission to help 1 million people reduce risk in their lives. As we conclude, Thomas, I want to thank you again for joining our mission. And on behalf of a Stotz Academy, I hereby award you alumni status for turning your worst investment ever into your best teaching moment. Do you have any parting words for the audience?
Dr. Thomas Powell:
You know, I go back to my kids. When my kids, I have five kids, so when the youngest one, I'd say, learn ope other people's experiences. So when you see your sister, your brother do something really stupid, don't do that. So this is a great opportunity, because we don't learn from the wins, we learn from the failures, right? So the ope is just an amazing way to do it,
Andrew Stotz:
and that's the way to reduce risk in your lives. Well, that's a wrap on another great story to help us create. Us create, grow and protect our wealth. Fellow risk takers, let's celebrate that. Today, we added one more person to our mission to help 1 million people reduce risk in their lives. This is your worst podcast host, Andrew Stotz saying that I will see you on the upside. You.