top of page

Lessons from Losing it All, and Then Making It All Back

Updated: Sep 15, 2022


Note: transcription provided by Otter.AI, which is a technology company that develops speech-to text transcription and translation applications using artificial intelligence and machine learning.


Christopher H. Loo, MD-PhD: Today, I have a very special guest, his name is Jeremy Delk. And he's a father foremost, he's but he's also a very successful entrepreneur, investor and speaker. So he's going to talk all about losing it all, learn lessons learned from the failures made, and you're going to come away with this show. very inspired. So I'm really excited. So Jeremy, welcome.

Jeremy Delk: Thanks for appreciating it. Thanks for having me.

Christopher H. Loo, MD-PhD: Yeah. We were talking backstage and hearing your story, it's very inspiring. So tell the listeners your journey. And we can go from there.

Jeremy Delk: Yeah, no, I appreciate it. And I'm really excited to learn a bit more about your audience and physician space and kind of, I think the niche that you're speaking towards, and helping - the people that help us right. I think it's so it's so admirable and crucial. So hopefully about a bit of experience in the healthcare space, really good and bad, and ugly, but I think you'll definitely take some away from it, and so will your listeners.

I'm a small town kid from Bardstown, Kentucky, we’re the bourbon capital of the world, just south about an hour south of Lexington, where I live now. I was on Wall Street, I had this affinity to want to trade. So I started trading stocks at a very, very young age. When I was 17, 18 years old, I was day trading. This is the late 90s. Then everyone who follows the economy knows what happened in the late 90s with the stock market. I grew a portfolio for about 30 grand to 3 million and lost it in about three and a half days, which was a lot of fun. A lot of lessons there, not while you're in it, but retrospectively, I think it helped shape my career.

Went and did a career in finance with a little company called Fidelity Investments in Boston then in New York. Was making a ton of money after digging myself out of that hole that I blew up, the portfolio. Making a lot of money, having the time of my life as a young individual in New York City, but found that I wasn't fulfilled. And I think that may even resonate to a lot of your audience that yeah, I've got the nice cars and the spoils of life. But I was going to work every day with all these ideas. And I was young in my 20s and passionate about working for that big organization. Sometimes it's very much like new ideas aren't necessarily welcome. It's like just keep your head down kid and it'll be okay. And I think that will probably resonate with some of your audience and, hey, I'm paid well, and your physicians are taken care of. But most physicians I speak to got into medicine to help people back in the day. And I think sometimes with this three piece system, between the payer, provider and patient, that's the law.

So for me, it wasn't healthcare, it was finance. I went out on my own and started Delk Enterprises about 20 years ago, and never looked back. Delk Enterprises is a small boutique venture capital firm. It's my money, I do co-invest with some. We do passive stuff, I was early in Uber, Airbnb 23andme. Most of our investment portfolio is either doing early stage startups ourselves, acquiring 100% or at least 51% control, and then trying to bolt them on into our little ecosystem. Evolved from real estate development, building materials into healthcare probably like the last 10 years so I can go into a lot of depth there and I've done a lot in healthcare. Some I'm really proud of, some that kind of cost me a lot. But nonetheless, really excited for the journey I think that I kind of put a mark on health care to some degree.

Today I found myself, we just exited one telemedicine concierge business actually I just exited. So now, I'm doing a lot of speaking and going through. And someone much smarter than me kind of said, Hey Jeremy you don't value what you know because you know it. And it really hit me because I always want to try to help. And my big thing, my drive for me, my passion is always learning. And now I speak to some of my coaching clients, and folks that I'm meeting with the invest in their companies, they're they're hitting these roadblocks that while you're there - back to me as a young kid losing millions of dollars - when you're in the moment, it's so hard to really look outside of it. But we all are human, and we're all natural. And we have this resilience to overcome adversity, but it's hard to remember it when you're in it.

So that's where I think I've been able to add a lot of value to some of my clients. I kind of go through and look at either investing in the business, buying the business, or just doing some business coaching with them. Let's really go through and dive down to, what is the actual core problem? And what happens if it isn't correct? What do we do? What's the move? And trying to think that more from a calm perspective, just because I've been through so much, and I've faced those tough times, and I've been able to come out the other side. So I think sharing that, and being that rock, as even a sounding board, sometimes helps.

Christopher H. Loo, MD-PhD: Yeah, that's a fantastic intro. And a lot of points resonate, the same thing. And I think a lot of the listeners are really piqued and intrigued by how you got started. And a lot of the listeners may be interested in, for example, the private side of investing, real estate and syndications, angel investing and venture capital. How did you get started in finance, what brought you to it?

Jeremy Delk: So at a very young age, growing up in a small town in the USA was great, but I just had this aspiration to see more and do more and go to this bigger city. Life in New York was that epicenter, and you watch any movie about New York, and a lot of times it isn't around finance and Wall Street. So that was kind of that first drive for me, I started looking and reading the Wall Street Journal, young and my father passed away when I was about seven years old. And I think that's shaped a lot of my ambition and my drive. And I came into, like a $30,000 inheritance from him that my mom had put into Disney and 20th Century Ultra mutual funds, which are great investments, but not something that excited the young Jeremy Delk.

So I started reading. This is like the early days of the Internet and Raging Bull. I don't know if it's even around anymore but like, message boards and like, just like the early early days, and I was much more interested in the high flier tech stuff, right? So JDS Uniphase and Qualcomm. That's where I learned my investing bones. The hard way, right? I learned that you're not always invincible, and that education is crucial. I was making a lot of money, millions of dollars at a young age. In a bull market. Everyone's a genius, then, right? I think right now you're looking at things like oh, well, maybe it's just not as easy as throwing it through there. So when I lost everything, I gained a lot of market depth and knowledge just from experience. When you're in it, in that micro component, day trading. And that's what afforded me to become the - at the time, I don't know if I've been replaced. But at the time I was the youngest broker and trader in Fidelity's history. I got licensed with my series 763, at 20 years old. And I only got that shot just by chance, meeting one of the head traders at a cocktail party. And he's like, how do you know what you know about the market? because I just had that knack for it. I was following everything. And even if I wasn't trading in that sector, I had a good understanding of what was going on in the piece and experiences will get set, you can't really read that you just got to really just inundate yourself. And it was funny, after losing it all, actually reading and learning licenses and going through and understanding my debt, finance, hedges, all these. I was completely naked on all my - I mean, I could have the things I could have done to save that portfolio were so basic and disciplined. But Hindsight is 2020 and you don't know until you kind of go and retrospectively losing that money is probably the best thing ever happened to me.

Christopher H. Loo, MD-PhD: Yeah. And we all go through journeys. What particular lesson, in terms of losing it all, was the key takeaway from that experience?

Jeremy Delk: Well, I think it just goes back to like this resilience piece, right? I've got a book that I just finished a chapter on. It'll be out later this year. It's more of a memoir, but there's definitely my business lessons in it. And the title is Without a Plan. And it's a memoir of taking unbound action and failing my way to success. And I think failure in our society, especially even in school, instills this bad thing and this negative component, and I just really cannot disagree more. I mean, like, I had this healthcare company that was the 24th, fastest growing company in the US by Inc 500. Number four, in healthcare. That's a cool accolade, and stat. Many didn't learn anything from that award. What I learned from all this stuff, getting there, right, and failing and falling out, and just that resilience of kind of keeping going. I think that's the biggest lesson I've had after that, right? We've had a very regulated industry, and we had some issues from a regulatory perspective and paid a bunch of money. And, and I'm still here as well, right?

I think that's the biggest piece, while you're in the moment, you have to know that this too shall pass. And the important piece is not not making the same mistake twice. It's okay to fail. And it's okay to make a mistake. But really learn from it and take it through because that's the magic. That's the really important part of where you dig into like, understand, like, Okay, how do I apply that? And that's why most people that you see, they've been in business for 2030 years. They're not oracles, they've just seen a lot. And they've failed a lot. But you won't ever see or learn those things unless you get started. I think that's the biggest thing that I do in my coaching now. And I think my passion for my book is just to really let people know that it's okay, right. Embrace failure. I tried to fail fast. I put rules on failure going through. So I can go through, have these micro failures, because that's where you really learn, as opposed to having this well thought out, methodical plan with a 27 point strategy. Why do it? Because it doesn't work, right? Show me a business [that has] the executive plan, show me one. Netflix? Has Netflix got a plan? I don't get DVDs in my mailbox anymore, right? They pivoted.

You go through and waste all that time. And it's all theory. The best thing to know is when you're actually in it, going through and talking to a customer, to a patient, that's when you learn. And that's when you can be adaptive. And I think the program, at least my side, tends to have a better result. Because if you have this very diligent plan, because you're going through and saying, Alright, well, at this roadblock, I'm supposed to do this, because that was my plan. If you don't have a detailed component, you can be much more agile and fluid and say, hey, well, this is the information I have now. These are my options, and you're much more decisive, and you're less.. Human nature is going to make you want to try to make that plan work. And so many times I see these entrepreneurs square peg - round holing it. I'm like, Guys, look, isn't this an easier path? And if they didn't have that preconceived notion, they wouldn't be in their own way.

Christopher H. Loo, MD-PhD: Yeah. It's like, it's like what we're going through now: the markets, the equities, the crypto markets and people are just getting wiped out. And it's basically washing away all the weak players. And then there's lessons to be learned and strategies moving forward. So just take what you take from the lesson and then move forward. And, and then that's why you were able to come back much stronger.

So you have this setback, you have this failure, but you took the lesson. What opportunities helped you to climb back to the top?

Jeremy Delk: You have to be open, life is a journey, I firmly believe that life is the journey, not the destination, right? And you have to be open to the journey. I think that personal life, maybe some, there's some anomalies to this, but I'm 100% confident, in business, there's no such thing as a good thing or bad thing that happens to you in business life. It's the emotions and the actions that we lay out to those events that will determine if they were good or bad. So to answer your question, it is just a natural progression.

If I didn't blow up that $3 million portfolio, which taught me nothing always goes good forever. You're not always the smartest person in the room. You're not invincible. So many lessons that I learned from there, what's the worst that could happen? The worst thing that could happen was I could have gone home and lived with my mom right after college. Like once you understand those pieces, that's that component. But then you have to look at where the journey takes you. Had I not lost that. I wouldn’t have been renting apartments at a side gig to try to cover my condo bill and met that head trader at Fidelity. And then it wouldn't have led me to buy Austin as an Institutional Equity trader, to move to a city that I always dreamed of as a kid, in New York.

So you have to appreciate that there's a much bigger component that's happening. You'd have to be open to receiving it and say, Hey, let's try it. And it always doesn't work out. Who cares? Now move on, like living in regret and living in woulda, shoulda coulda. It's no fucking way to live, man. You just have to be open to try it. And, set boundaries, right? I mean, I'm not saying presuppositions are saying, Hey, this is great inspiration, I'm gonna go out. And I always want you to knit sweaters. Like, that's probably not what you should do. But try and knit a sweater.

Go through and just make those micro steps to just get started. And then see how it goes to stick your toe in. All right, well, maybe I can expand, I can go through and see if I can take it to the next level, the next level, but it's just a constant desire to continue to learn and be open to the lessons that are being taught to you because nothing's happening at you or to you, right? So we have to change your mindset, it's not happening to you. There's a reason these things are happening.

Christopher H. Loo, MD-PhD: Yeah, that's fantastic. And for all the listeners all this is very inspirational. But you Jeremy, you mentioned that you are a venture capitalist and you look at upcoming startups. A lot of physicians are actually interested in passive investments particularly real estate syndications. But there are a subset of people who are interested in the startup world with all of these upcoming technologies. So tell us more about your work.

Jeremy Delk: Yeah, I mean, I practice what I preach, right. I've got a beach house, down on if you're familiar with the British Virgin Islands, but a small little island called Yoast Van Dyck. If you listen to country music, Kenny Chesney is down there all the time. And he's been down by the house and sings about Ivan's and what have you, I was down there. And I built a house on a very habited Island and that I actually rent it out for passive income. I have not been there, because I had to kind of work as well. And I built that house four years ago in the middle of a hurricane. And I haven't made a mortgage payment personally, in four years, something like that. We were looking at expanding then obviously COVID happened. I was down in the islands. This is November of this year, a very small community. And I had some friends down. We were going out to Necker Island, Richard Branson's place, and just hopping around islands. And a realtor buddy and someone in government said, Hey, Jeremy, this guy just bought this resort. He’d like to meet you. Maybe there's something you guys could do together. So I said, Sure. I just said yes. No, I just said yes.

And he said, listen, we got to gas up and get supplies at Tortola, meet me at the fuel dock, run me over and I'll check out the spot. I've literally been there one time for half an hour in board shorts and a T-shirt. And I'm, we're down in league final legal diligence. And I'll probably end up buying 20% of that resource. And developing 15 to 21 to $2 million villas that we will sell is an already operating resort. And that will sell to investors that go through and get passive income like I did, I'm going to make a few million dollars out of that deal. I'm going to have fun, it's another place to go. They've got a great sushi restaurant, it's got a half a mile private beach. If I would have said no, I've got this plan. I wouldn't see that opportunity.

Now. It doesn't always go that way. But that's where you have to be open to open and see where it takes you. And just be curious. That's that for me, I was going through another deal. I got a meeting here and 20 minutes after we wrapped with the guy that's got a SaaS company in college student housing that we're looking at doing. He's built a business, he's got some revenue, it's at an early stage of less than a million dollars in annual revenue. But SaaS companies trade at 20-30 times multiple if you can get some scale. I have a lot of resources that could help them out from a marketing endpoint. So I look at anything and then I'm just really quick to say even failure like yes, I can help or I can't because I can't do everything. I've got a very specific niche I can go through and help and I've been fortunate that I've had a lot of good deal flow that comes through to me.

Christopher H. Loo, MD-PhD: Nice, nice. Yeah. Well, we're coming up on time, but I know you have a book coming out. So tell the listeners about your upcoming work and then how people can contact you. I'm sure a lot of physicians are really interested. I was really inspired by this talk and how they can contact you and follow you work with you.

Jeremy Delk: Yeah, for sure. is the website I'm @JeremySDelk, all social. So Twitter, LinkedIn, Instagram, Facebook, all of those things. And I've got a simple link, you can jump on and book a call with me to chat. A lot of these things, I do some coaching, a lot of those have been really mutually beneficial for myself and the industry because it allows me to do some diligence. And it's led me to a couple of deals where I've actually bought a company or invested in a company. So that's kind of a neat piece. And if it doesn't lead to that, hopefully, they leave with some really good lessons in some takeaways.

The book man, if you've ever written a book, don't recommend it, it's a therapy session, all packed into one. We're getting close, we're hoping to be done at the end of this year, so it should be ready and on stands by Christmas. I'll try and leak you out a couple chapters that you can kind of share as they come through and live chat to you. But it's it's story of my life, that's really how I live in the title. It says it all without a plan. And this is not saying you can live through life, aimlessly, lollipops and gumdrops, it's all going to work out. But just go and get started and go through and enjoy the ride. And that's what life's about.

I think for your physicians that are going through it. I think that's really something that you're, you're already doing such a good job by giving them that component of like, Hey, you're at a point in your career, you're helping people and you're burnt out or whatever. What's your why? I mean, I was making so much money. And that doesn't always mean happiness, right? Like, What's your why? For me, it's my kids. It's being a good father. It's travel, it's those things, good work and investment returns help pay for and afford a lot of those things. But you gotta get down to your core of what your passion really is. What do you want to do? And it needs to be authentic. It needs to be what's important to you, right? Not your neighbor, not Joe? Not Chris, not Jeremy, what's important to you? And focus on that. And that's all that matters, man.

Christopher H. Loo, MD-PhD: Yeah, so well said. So it's been a really great conversation. I really enjoyed it. And for all the listeners, Jeremy's resources, links will be in the show notes, and we look forward to having you as a future guest on the podcast.

Jeremy Delk: Thanks so much. I really appreciate it.

Christopher H. Loo, MD-PhD: Many thanks again for being here. If you’re new, you can find me online at Christopher H. Loo, MD-PhD, where I have links to other episodes or links to online resources that will support you on your financial literacy journey. I’ll see you there in on next week’s show. While I bring you thoroughly vetted information on this show regarding a variety of financial topics, I cannot promise you a one size fits all solution. This is why I caution you to continue to learn. Educate yourself and seek professional advice unique to your situation. If you want to talk to me, I welcome it. Please reach out via my website or email at I read and personally respond to all of my emails. Talk soon!


Editor's note: This transcript has been edited for brevity and clarity.


bottom of page