What does it take to transition from a Wall Street powerhouse to one of the rising angel investors shaping the West Coast startup scene? In this episode of Success Unleash’d, Shawne Merriman and Zack Ellison sit down with Evan Dreyer, a former NYU classmate of Zack’s turned investor and operator, who shares his journey from Credit Suisse to angel investing at Halo Labs to supporting small business innovation through supply chain financing at TOLA. Hear how Evan’s unique blend of risk management expertise and entrepreneurial spirit landed him a full-time role at one of his own angel investments. Plus, Evan opens up about how his athletic mindset—honed during his grueling college football days—has been a game-changer in the high-stakes world of startups. Whether you’re a budding entrepreneur or just curious about the grit it takes to succeed, this episode is packed with insights you won’t want to miss.

Success Unleash’d Principles From This Episode

1. Pursue Opportunities with Conviction

Evan emphasized the importance of identifying opportunities that align with your expertise and passion. He joined TOLA full-time because it aligned with his domain expertise in risk management. His leap of faith underscores the power of conviction when pursuing the right opportunities.

2. Leverage Your Strengths to Add Value

 Evan’s transition into operating roles showcases how leveraging your unique skill set – like his risk management expertise – can create value in early-stage companies. This principle applies to any role: find your strengths and use them to make an impact.

3. Adopt an Athletic Mindset

 As a former college football player, Evan credits his athletic background for teaching him resilience, discipline, and the ability to handle setbacks. The “no failure, only lessons” mindset is a cornerstone for success in both sports and startups.

4. Balance Relentless Effort with Strategic Pivots

 Evan discussed the importance of pushing hard toward goals while staying flexible. When plans don’t work, leaders and founders must recognize when to pivot without losing sight of their ultimate mission.

5. Start Your Week on Sunday

A powerful productivity hack from Shawne Merriman: treat Sunday like Monday. Preparing for the week ahead on Sunday ensures you start Monday with momentum, ahead of the competition, and in full swing while others are still catching up.

6. Build Relationships Based on Trust and Shared Success

Evan’s experience as an angel investor highlights the importance of aligning incentives and building authentic relationships. Trust and a long-term perspective can create opportunities for collaboration and mutual growth.

7. Be Willing to Put Yourself Out There

Whether it’s taking calculated risks or tackling challenges like removing lead cables from Lake Tahoe, Evan stressed the value of stepping out of your comfort zone. Real progress often comes from bold moves and persistence.

8. Focus on Long-Term Value, Not Just Short-Term Wins

Both Zack and Evan highlighted the importance of avoiding short-term transactional thinking. Whether in angel investing or building relationships, aim to make the pie bigger for everyone involved rather than focusing solely on short-term wins.

9. Be Relentless While Managing Energy

Evan discussed the importance of having a go-all-in mentality but acknowledged the need to pace yourself. Founders and leaders must learn to scale back at times to avoid burnout while maintaining their drive and determination. Taking breaks to reflect and recharge can amplify long-term performance.

10. Turn Failure into a Stepping Stone

One of the recurring themes in this episode is the importance of viewing failure not as an endpoint but as a stepping stone to success. As Evan said, failure is a signal to work harder, learn from the experience, and come back stronger. This mindset is crucial for navigating the ups and downs of entrepreneurship.

These principles illustrate that success isn’t just about talent or opportunity; it’s about grit, adaptability, and the ability to foster meaningful connections. From athletes to entrepreneurs, the lessons shared in this episode are a roadmap for overcoming challenges and achieving long-term success.

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Listen to the Podcast Here

From Athlete To Angel Investor: Evan Dreyer’s Journey Of Risk, Resilience, And Building Success

In this episode, we have with us Evan Dreyer, who is my good friend and former NYU classmate and is becoming one of the leading Angel investors on the West Coast. Evan, thanks for joining.

Thanks for having me, Zack. Becoming a leading Angel investor, we have a long way to go. It’s a long-term game.

Evan, tell everybody what you’re doing full-time and as an Angel investor. We’ll then dig into how you got here.

Evan’s Transition From Angel Investor To Full-Time Operator

I’m focused on the early stage as an operator and investor. The lines are a little bit blurred because I joined one of my investments full-time. My Angel investing career led to career opportunities. I invested in a company by the name of Tola back in 2022. I got close to the founders. I was giving them some perspective on risk management and how to build things from scratch. They gave me the opportunity to come aboard full-time and I took it.

I’m our Head of Risk. We’re helping small business owners get paid and access financing. We built a proprietary supply chain financing offering. We’re working with all different types of businesses like wholesale, retail, and restaurants, real main street businesses, and get to work with entrepreneurs every day. People are starting things from scratch and are doing it on their own. It’s been a great journey.

We’ve done millions of dollars in supply chain financing for these customers and raised over $10 million from Sequoia, Y Combinator, Creandum, and Cherry. It’s been a great experience. I’ve done a ton of Angel investments. I invested in over 50 companies over the years and I’m happy to dig into that journey for sure.

You invested in 50 companies. What were you looking for when you decided to come on full-time with the company? What separates something that you wanted to be a part of yourself as opposed to the other ones that you thought were good businesses you invested in?

I would love to work with more closely with other companies, for sure. The opportunity was so unique because it was something that was specifically in my domain expertise of risk management, where they needed to build risk from scratch. The founders were incredible products people and experienced people in technology. They had great backing and fundraising. It had a market that I was intrigued with. It was that opportunity, the team, and the funding.

It’s a little bit different opportunity when you’re joining a place that’s had a successful early-stage fundraise. The thing with me is I’m always trying to do what I’m given a perspective on or given advice to. I was always saying, “I want to join a technology company or someplace and build risk from there.” The opportunity to do it from scratch before we had a customer. When I hopped there, we didn’t have a single customer yet. I had been given the perspective, “Here’s how you do it.” It’s one thing to talk about it. It’s another thing to roll up your sleeves and do it. I couldn’t say no to that opportunity.

When we first met, you were working at Credit Suisse, if I’m not mistaken. You had graduated from the University of Chicago, where they say fun goes to die, but only in undergrad, not for business school.

We had a little bit of fun. I played football there in a completely different galaxy than Shawne. I grew up as a Raiders fan. It is nice to meet you but you were a terror for me earlier in life, going after Andrew Walter. I get flashbacks but it’s great to meet you. I was a right tackle. I was an Economics major. I’m from Sacramento originally. Going to Chicago, I didn’t know a single person there. I had been there for family stuff, but it was an amazing opportunity to be a student-athlete and learn a lot about finance.

My parents are lawyers. I didn’t know a ton about finance. Wall Street was always this dream and you go there. I showed up there in 2006 or 2007. All the guys on the football team were getting $150,000 a year jobs. I’m like, “What’s this Wall Street stuff?” That’s the peak crisis, as we know now. There was some crazy stuff happening but it was a unique time to be pursuing that path.

The Role Of Athletic Mindset In Entrepreneurial Success

Being a Raiders fan, I’m happy that you accepted to come on this interview because that doesn’t happen too much from Raiders fans. You played football. I got this thing with athletes. I feel like as athletes in general, in my opinion, it doesn’t matter whether you played at the highest level, college, D1, or D2. You went through a training camp.

You’ve had your fingers slammed in between two helmets and jammed some thumbs. Your feet were stepped on in the cold. You know what that feeling is like. Did you apply any of that same mindset to this? I always had this thing with athletes. We approach everything a little bit differently than everybody else. Have you been able to use any of that from your athletic background?

I’d say most of it. It’s only then that I realize that some of the successes that I’ve had have been because of that. There were no lessons and silver linings. It’s just trying to get to the end. There’s a lot of different stuff. Athletes are used to pushing themselves perpetually. You’re used to that. There’s no real failure as an athlete.

If you try to lift the weight, you endeavor, or you set a PR. If you drop it, it’s not a failure. It’s like, “I got to get stronger and do some stabilization muscles.” You’re always used to pushing yourself, never being complacent. If you win a game, it’s like, “Let’s go to the playoffs. What about next year? Can you do it again?” Being a professional and also an entrepreneur is something that when you grow up that way where it’s always going for it and pushing it, it doesn’t leave you.

Has it been an adjustment? We’re so used to pushing ourselves to the limit. You haven’t pushed yourself until you’re running half-gassers in the heat at the end of practice. There’s 90-plus degrees humidity. You got nothing left and you got three more. If you jump offside, you have to start all over again. This is a different mentality. Has there been an adjustment to your mentality, not matching up to other people and trying to be around more like-minded people to have that same attitude as you do?

I try to use it as an opportunity to lead and be like, “We’re going to be okay. We fail. We have a loss.” Even with great teams, you have that stuff. A good team that has an eleven-game winning streak lost. It’s like, “What do you do next?” That’s a big thing when you go to Wall Street, especially the era I did. Founders starting a company. You get a lot of people from the Ivy League or people who are 4.0 students. They’re not used to it.

Being an entrepreneur, as both of you know, stuff’s not going to work. You’re going to have those situations. “This is the first time I’ve ever dealt with it.” No, you go. I try to bring that mentality to people and share that. There’s another opportunity coming around the corner. It’s a lot of the stuff that maybe my coaches said back in the day and I’d listen, resonate, or even sometimes roll my eyes. Now, I appreciate that. Failure is a sign to work more, not less.

Talk a little bit about your rise through Credit Suisse and then what made you want to transition into working with early-stage companies.

The Financial Crisis And Career Beginnings

That could be a long conversation but for me, I bring up going into the financial crisis because that was a big thing. In 2010, when I was graduating college, I didn’t get it. I was interviewing for jobs and it was lots of noes. I got rejected from a lot of different places. For me, this is a relatively new dream, to try to go and be in finance. I love data and stats. I was an Economics major. It was the opportunity there to be working on big-time things. It was something I didn’t give up on. The market turned a little bit in the spring of 2010. I got an opportunity.

I was going for investment banking which wouldn’t have been the best place for me right out of college. The market opened up. I got this job in capital markets, which was perfect for me. You’re covering companies. It’s a lot of hard work but also connected to the trading floor. That guided my career from there. You follow the market and go where there’s opportunity. You don’t try to force, “Here’s what I want. Here’s what success looks like to me. It’s got to happen this way.” You go operate with more generalities. You have that goal. If you get a little too particular, you’re going to be let down once you get there.

At that time in 2010, Credit Suisse was maybe the best bank on the street. It was only the big bank that didn’t take any money from the government. We were in a good position. Ironically, I got to see Credit Suisse go from one of those top places into a challenging spot where a year after I left, the bank was no more. They had gotten acquired. I got to see an interesting life cycle.

I had a very untraditional career in finance. I hopped in on capital markets, but I let the market lead me. I was on a big M&A deal and ended up joining the M&A team. They were trying to start a new team focused on hostile takeovers and shareholder activism. Maybe that wasn’t what everyone had said. I said, “That sounds pretty cool to me. How do you go back at Carl Icahn and Bill Ackman to deal with these guys?” That was early in my career. I got those opportunities to go to unique roles and build teams.

Everybody deals with rejection a little bit differently. I always bring it back to the athlete mindset because some days, you are going to get your ass kicked in practice. I’ve played against some all-pro-offensive linemen in practice. We had one on the team. They threw me around for a couple of days. Rejection didn’t bother me. It had me to button up, tighten up, and lace my boots up to get back to it. How did you handle that rejection when you were going to job after job and you didn’t get it? What was your approach after that?

Handling Rejection And Maintaining Determination

You keep grinding. That’s athlete mentality. If you want it bad enough, you’re going to keep at it. It is what it is. Sometimes those rejections are like, “I’m off track. I’m off the right path. There’s a reason this isn’t working.” I have some examples of that. You were trying to force something to be true that isn’t. You have to have a good relationship with yourself. That’s the number one thing. If you want to pitch people or come across a certain way, that’s one thing, but you’ve got to be real with those conversations you have with yourself. Those kinds of rejections were like, “I want to make this happen.”

In the spring of my senior year, there were a lot of parties and fun. I was in the career office talking to people and sending out emails. I was doing it because it mattered the most to me. If you never give up, you can’t fail. It’s how I view it. That’s what I tell founders now. Refuse to give up. There are always reasons to give up and why something shouldn’t work out.

That kind of mentality is a lot of what I look for at the early stages. One of the big criteria I have for Angel investments, for example, is would this person rather fail doing this than succeed in doing something else. If they feel that way about their company and idea and they keep that mentality, they’re eventually going to be successful.

I like what you said about following the market and taking what it gives you. That’s broadly applicable to life in the sense that we don’t know where life’s going to take us, but if you’re paying attention to the markets and your opportunities in life, they are going to come about. You have to be ready to seize them when they’re there. You can’t force the action. If the market’s going down, there’s not a lot you can do about that, but you can position yourself for success in any type of market.

The refrain we heard a lot a few years ago was don’t fight the Fed. That was always a profound thing for me because when I was at U of Chicago early on, the industry environment was completely different. What the Fed did in the majority of my career was unprecedented. A lot of people were waiting for the market to go back. “It’ll go back next year. Interest rates will bounce.” You might have missed the biggest opportunity of all time of having near-zero interest rates.

The people who looked at the market and didn’t fight the tide and embraced it had those opportunities. That’s something I’ve always tried to guide. You want to impose your will on stuff and make certain things happen. Shawne, you’ve seen the game change so many times and you’re one of the first guys who was bringing a ton of strength and speed to that defensive end position. You look at it and there are a lot of guys. That’s the prototype. What’s next? Do you want to go after what has been or after what’s next and be at the top of that curve?

I’m laughing because only athletes say, “Impose your will.” It is so common with athletes. You don’t hear that anywhere else. You don’t hear it outside in a job atmosphere or in what I like to call the civilian world or the people who didn’t play sports or weren’t an athlete. How important is that? Everything is not going to go your way or go the place you wanted to go, but imposing your will is something that I always say. When you impose your will on something, it’s almost irrefutable. You can’t fight it. You’re going to go for it no matter what. How does imposing your will on what you’re doing become important to you?

Conviction And Imposing Your Will In Business

It’s conviction. When you’re investing in companies and people, imposing your will, in maybe a more classic, civilized world way, is conviction. You want to make sure you believe in something. What are you willing to risk to get that? What are you willing to do? Especially in the Angel investing world, people are like, “Anytime you need something, I got you.” Will you pick up the phone?

Imposing your will is about confidence and conviction to be like, “This isn’t something that’s breezing in the wind. I want to make this happen. I’m willing to put myself out there and try to make it happen.” A lot of the things I’ve done is hopped in a lot with the customers, put myself out there, demoed the product, and talked about it like, “This can help you. I know it can.”

When it comes to sales and stuff, I’m not a sales guy. We can get into why I was doing that. To me, you want to bring that. For other people, when they see someone who’s convicted and confident and they see that belief and it’s real and not BS, when they feel that person who’s got a will and they’re trying to make something happen, they’re going to follow that person. They’re going to want to be involved and get behind that.

A lot of times, in Angel investing, you deal with companies and stuff that are not working. People are questioning themselves, the direction, and their relationships within the company. When you try to bring them, it’s like, “What do you believe in? What are you trying to make happen? Let’s do it. Let’s go and make that happen. Let’s not worry that this little thing didn’t go well. Who gives a crap? Let it rip. What is the goal? What are you trying to build? Is that stopping you from it?”

That’s the same thing. Maybe you lined up wrong in a play. You’re in the wrong gap or you mishear something. You get blocked at that first pump. You sit there and collapse. No, you get going. You grip, claw, and try to make something happen. You don’t give up even if, initially, it seems like it’s not working. It’s a nightmare for offensive linemen.

This is where a lot of you guys made a major bread. “I’ll get that good first punch. If the guy’s got a motor and he keeps going and he spin moves and that quarterback’s dancing around back there, every second that passes, your chances of winning is higher than mine if you keep going.” That’s the mentality. When you’re trying to make something happen and go get it, that’s what you want to do.

Balancing Relentless Pursuit With The Ability To Pivot

I want to ask you about how you balance this relentless pursuit and high conviction with the ability to pivot when things are not going to work out. You always come to that place as a founder. Almost 100% of the time, every founder faces that dilemma where it’s like, “Do I keep going and go all in, even if it’s probably not going to work out or do I pivot and admit that maybe I was wrong and I’ve got to go in another direction?” How do you find that balance?

You got to be able to try stuff. For early-stage companies, you have to be willing to give it a shot. For larger companies, it’s a lot of strategy and discussion. A lot has to happen before a decision is made. A lot of people need to be involved in that decision. You have to play the ball wisely. Let’s use another sports analogy. If something’s not working, try something different. Don’t keep pounding your head against the table.

In terms of making things happen, what is that ultimate goal? I’m trying to help small business owners. If that’s my goal, there are a lot of different ways to achieve that. A lot of times, it gets back to that. You put together a business plan. How often do you refer to that over the first three years? The work in the business plan is collecting your thoughts. Once you’re out there on the field, you got to play fast and loose so to speak.

When you’re pivoting, you have to take the information as it’s coming in and make new decisions. A lot of times, you want to be accountable. This is the balance you’re talking about. “Here’s what we’re trying to do.” When you’re getting new information, you have to be willing to do things. There are a lot of different examples I can give. I’ve been involved in this environmental project up in Lake Tahoe, where we got 6 miles of lead cable out of the lake. That was the only goal.

The reason why that effort was successful was our only goal was to get that lead out, not like, “We got to do it this way. This group’s got to do this. This person’s got to say sorry.” When you get overly prescriptive, you run into trouble. The goal is to win the game. If you win by 50 points or 1 point, winning is winning.

Managing Personal Energy And Scaling Back

I hear your voice and you like to go. That’s me. I’m going to push as hard as I possibly can to point out words almost like unsafe. It’s not healthy. I don’t know if it’s an athlete thing or it was something I was born with. When I played ball, that was the only thing I knew. At what point do you scale back? When you’re starting something, you’re an entrepreneur, you’re starting a business or a company, you just want to go, but there’s a certain level of going and having to scale back so you can revamp, re-anchor, and get back going. Do you start setting times where you’re like, “Let me scale back before I burn myself out?”

The go mentality has to be for you. Where you get into trouble is when you expect that out of everyone. You want to motivate people and help people. However, if you’re hard-charging, if someone doesn’t want to work like you do, and you’re working with someone and jamming them up, it’s going to lead to problems. I try to harness that more. When I was younger, I let it rip and go. If I piss some people off, so be it.

Over time, as I’ve dealt with more people, I had some interpersonal challenges in work and in corporations, you learn that. You also have to make sure that you’re not taking away from someone else’s approach. Not everyone is like you. I’m sure you played with guys who were mellow-mannered. They were yelling, hooting, and hollering but when it came down to game time, that’s a guy you want by your side. Not everyone has to do it your way. That’s more of a freedom thing in general. I try not to impose my will on how other people got to act. The only will I’m trying to impose is my own.

That’s what football helped me out the most because you have all these different personalities. I was a rah-rah guy. I came out of the tunnel last. I broke into huddle down. I got everybody going. It was guys listening to gospel music on the way to the game. I was like, “We’re about to go commit acts of violence here for 60 minutes and 4 quarters. You guys listen to gospel.”

What it did for me was I was able to understand how everybody works. I’m listening to Little John or something I would bang my head to before the game. I’m going out rowdy. I want to go. You have some guys who are calm, cool, and low demeanor, and yet when that ball snapped, it was on. To everything that I’m building, I take that same approach. Everybody has a different way of getting there.

You’re right. I roll out the bed, ready to go. I don’t need any motivation. Nobody say anything to me to get me pissed off before the game. I’m already pissed off. You don’t have to. I’ve already told myself something for me to piss myself off. I walk into the stadium pissed off already and everybody’s not like that. Have you been able to take any of that to what you’re doing now?

Leadership And Communication In Team Dynamics

Yeah. For me, it’s like leadership. To get back on the career stuff more, I had an opportunity early in my career. Everyone in banking and M&A was going to private equity and hedge funds. I got an opportunity to go internally to an internal strategy team, which was working directly with senior management. At age 24, I worked with business leaders and people running the show. That organically became my role in risk.

I saw a lot of leadership, good and bad, thoughtful enough, thoughtful early. It was in sports. One quote that resonates with me always was, “Leadership is a skill. It’s not a rank.” It’s about making people more productive. If you’re a leader, you’re reaching out to other people. You’re being you and staying true to yourself but when you’re working with teams, it’s like, “How do I help this person? How do I make that person better? How do I be someone who can help to get the most out of them?” Not, “Do what I say. Here’s the email and make it all so.”

Nobody wants to work with people like that unless they’re the ultimate high achiever and then they’ll burn them out eventually. When you work with people, you’re in that kind of mentality, and you’re in the trenches of people, you want to be there for them. A big thing with risk management is communication. Risk management about numbers. I watched a lot of numbers get produced and a lot of reports get written. They didn’t always get read. Do you know what doesn’t get lost in translation? Face-to-face conversations. You have to have that communication and line. You got to be someone that people want to deal with. In Angel investing, that’s huge.

If your Angel investor is barking down your throat about what to do and how to do it, you’re eventually not going to have time for them. When you do Angel investing, what I do, and it’s hard to do but you have to respect that line, is you try to add perspective, not give advice. A big discernment you need to make is, “Where am I? What seat am I at the table? Am I the CEO of this company?” No, so stop telling the guy like you are. You have to calibrate your mentality.

You don’t change who you are. You want to have that engine and motor, but if they line you up in different places or put you on other things, you want to conform to that. You don’t want to say, “I’m only this person 24/7.” Say,” I can be flexible, be on the phone with a customer, do the hardcore analysis, and present to different groups of people.”

You want to be someone still driven the same way. Your process is the same but when it comes to the medium and what you’re doing, you’ve got to know your audience and what is appropriate here because again, we’re trying to achieve something. It’s not more important for me to do things my way than for what we’re collectively trying to get done.

I want to ask you about leadership. Most people aren’t going to be leaders. By structure, there’s only a small percentage of folks who are in leadership positions and a smaller percentage who are doing a good job in those positions. Let’s talk to the rest of the population where 99% is not in a leadership position. What advice would you give to people, whether they’re employees or athletes, who are important to the team or the broader organization but they’re not leaders? What should they do to help even if they’re not in a leadership position?

That’s where I get into that. I view leadership as a skill. People can be leaders. Are you going to be the management or the decision-maker? No. You got to be real about that, but you can always lead and that’s doing your best at those types of things. You want to talk about ways to be successful and tangible things to do. If you’re in a position where you’re reporting to someone and you’re not the CEO, the number one thing you should be trying to do is make that person’s life and that job easier. Take as much of their responsibility as you can off their plate to free them up to do bigger and better things.

That’s something that happened in my career when I was working with people who were on the rise. I would make their life easier. I’d be doing their job in a lot of ways, so to speak. That didn’t lead to them sitting back and going on vacation. It led to them taking on more ambitious things and then they brought me with them. If you’re in that position where you don’t have the title on the business card, that person that you’re working with, bust your ass for them and make them look good. Maybe not day 1 or day 2 but eventually, it’s going to come around. When they look around for who’s next, they’re going to be looking to you.

Evan, we had this thing in football. I don’t know if you heard it or not, but we used to say, “The more you can do.” We have some of these guys who are late-round drafts and take 4th, 5th, 6th rounds, free agents sometimes. They’ll come to me in training camp in the first week. “Shawne, I’m trying to make the team. What can I do?” I said, “The more you can do.” You’re talking about taking a lot off the plate of a CEO and making yourself valuable. I tell these young guys when they come in, “Run down on kickoff. Special team, they need you. If they need you on scout team, go to the scout team. If they need you to carry these waters and helmets off the field, or clear up the locker room, do all of it.”

Do everything you possibly can to make the team because the more you can do, the more value you create for yourself. You don’t have to own a company, but you can also be extremely valuable by taking a lot off the plate of that CEO or upper management so they don’t have to worry about it as much. You create something for yourself and make yourself valuable.

Value In Doing More And Being Non-Transactional

I couldn’t agree more. I’m going to use that, Shawne. Another caveat I’d add to that is you can’t be transactional. If you go pick up something in the locker room and no one comes and says, “Thanks for doing that,” that can’t mean that you’re not going to do it the next time. When people push themselves and do extra, so to speak, if they don’t get those immediate returns, sometimes they don’t do it.

In the finance concept, that means coming up, spending all night working on a pitch that nobody reads or someone looks at for two minutes and throws down. Does that mean you never do it again or do you keep trying? Do more for yourself. Not because it’s going to get you ahead but because you want to operate on that job.

In most situations, people think, especially younger in your career, that you want everyone to be watching everything you’re doing and be like, “They’re a diamond in the rough or ready for the next level. Let’s do it.” In my experience, that’s not how it works. The only people who are getting promoted or getting into leadership positions are people who are taking it or people who are already operating at that job or level. You’re not going to get promoted to that next level.

Companies are risk-averse with promotions in a lot of ways. They’re not going to get you to that next level until they already see you there, then an extra stamp of approval. Maybe for injury or something but they’re not going to get made a starter. You’re going to have to be someone who’s breathing down someone’s neck and take that spot, not just, “It’s his turn.” That’s not how stuff goes down most of the time.

When you guys talked about this idea of not being transactional, to me, that’s one of the most important things. Many people in business are very short-term oriented. They’re thinking, “How can I profit right now?” They’re not necessarily trying to hurt their counterparty but they don’t give a thing about them. It shows. They’re trying to make as much money or power as they can in this one transaction. They’re missing the big picture.

I used to think a lot about this in trading. I was on the sell side making markets and trading with the biggest fixed-income investors in the world like BlackRock, T. Rowe Price, Vanguard, and PIMCO. You name it. That is a long-term game. When you think about the game theory around each trade, you’re not trying to maximize the profit on one trade. You’re thinking, “How am I going to benefit over the long-term with this relationship?”

If I screw over BlackRock or PIMCO on a trade, they’re going to crush me for the rest of my career. There’s this balance that you have to learn as a trader on the sell side whereby you have to make money the majority of the time or you’re not going to have a job, but you also have to make sure that your clients are making money. That taught me so much about business in general because, in every relationship that I enter into, I’m thinking about how we can both benefit. How do we create enough value between the two of us or amongst the group such that all of us are coming out ahead? Not me taking from you in a zero-sum game but let’s make the pie bigger like, “There’s one pizza. Let’s make enough money to order ten pizzas, then we can all eat and have as much as we want of any type.”

You want a relationship with BlackRock and PIMCO. You want them to be someone that you want to do business with. Someone who’s got to win every single trade, most of the time, that’s not who you want to deal with day-to-day. It gets back to that mentality of being willing to put yourself out there and fail. You don’t want to be penny wise, pound foolish. You don’t do everything to win the battle and lose the war. I’ve seen that in the startup world a ton. When it comes to growth, everyone’s got a plan on how it’s going to work and then when it doesn’t work, what do you do? You try stuff.

You make those phone calls, go to a conference, and try some ads. You do those small incremental things. “If the ROI doesn’t work on this, it’s going to be okay. Let’s get on to the next.” Do I want to jam? Do I want to lose my first-ever trade with PIMCO over a couple of basis points? Probably not. Get the job done. You want to be willing to try stuff. It’s that balance of you want to be a high performer but also you want to be able to try stuff. You want to have enough confidence to be like, “If this doesn’t work, we’re going to be okay, but I’m going to do things the right way.”

Embracing The Willingness To Try New Things

I don’t do things. Everything that I do is outside the box, which comes across as crazy. I’m like, “What are we going to lose? Just try it.” That’s all my attitude towards everything. Even when I started my business, we didn’t know exactly what was going to happen. I know I had the right team and the right ideas but I was like, “Let’s just try it.” I have worked with other big streaming platforms for years. I worked out of their offices. I’ve been around the TV space for many years. At what point did you get where you start thinking out of the box and trying things?

It’s that goal and strategy but willing to do that. An advice to my younger self type of stuff would be like, “Be more general with the goals.” Your goal is, “I want to put this together and have my fighting league. I want to stream it.” It’s not, “I have to have this advertiser. I got to have this.” It’s all those ifs and ands. When you’re setting goals, you want it to be general and something like, “That’s my goal. I’m willing to compromise along the way to get there because I know where I’m trying to arrive to.”

It becomes easier to try stuff then. My goal is not anytime I do something for it to work. That’d be great but that’s unrealistic. My goal is we’re trying to get more customers, for example. Try it. Talk to the person at the coffee shop and give them a business card. Is that putting yourself out there a little bit? Putting yourself out there is tough. For athletes, it’s a little different. You’re used to performing in front of people but high performers or people who are leaders don’t want to ever be perceived as, “This person doesn’t know what they’re doing.”

If something doesn’t work, you don’t know what you’re doing so to speak. You have to be willing to try it and go after it. If something’s not working, do not put your head in the sand but be willing to move. The people on your team see that mentality. I’d seen a decent amount of a highly competitive investment bank. When something’s not working because it’s someone’s career or idea, they want it to be perceived as a success.

Everyone knows that. People on the team can see through it. Maybe people externally can’t see through it, but chances are, if you’re on a team with someone and the person at the top is spending more time, showing the Peter Thiel thing of when signaling that good work is being done is more important than doing good work, game over. That’s where it is. You want people to know, “This person is trying to make things happen.” It makes it easier for someone else to try something.

When you go out and you try to do something and it doesn’t work and someone else on your team sees that like, “He gets up and goes next,” then when they fail or they don’t have something go, it’s easier for them to do that. That’s the type of culture. I’ve been in areas where everyone’s on pins and needles. If anyone screws up, everyone points it out. Those are never high-performing teams. Those are snake pits.

Incentive Structures In Decision-Making

Evan, I wanted to ask you about incentives. You talk about how decisions are made. What a lot of people don’t realize is decisions are made not based on what the best idea is. It’s based on the incentive structure of the people at the table making the decision. I’ve worked at 5 publicly traded companies, 3 of which have over $1 trillion in assets.

It’s amazing to me how slow they are to do things and how poor the decision-making is generally. They’re big enough to move slowly and make a lot of bad decisions and it doesn’t matter that much but startups, on the other hand, can’t do that. They will be gone. One of the things I like to think a lot about is how decisions get made. How do you get stuff through the hoop?

One of the things that Shawne is great at is he can get in the room with anybody and he makes things happen. There are people who have approached us all about partnerships, deals, this, and that. They want to talk. It drags on and on. It’s like, “Listen, let’s get this done.” Shawne and I are both very good at getting stuff done when it makes sense. Part of that is because we understand what the incentive structure is of the person or the people that we’re talking to.

We know how to put money in their pocket while also benefiting ourselves. I want to get your thoughts on incentives and how startup founders and business builders should be thinking about getting things done. It’s so hard to get things done when you’re starting. There’s this inertia. How do you create momentum and move the ball down the field?

The Challenges Of Being A Founder And CEO

I’m still trying to figure that out. What that tells me is it’s a little different for everyone. One of the biggest challenges with the founder, and you two are founders, I’ve done much smaller scale stuff than you, is it requires so many different skills. Where people get into trouble is they’ll get someone who is good at 1 or 2 things and they want to stay focused there.

Sometimes I’ll explain this as there are a lot of people who want to be founders and don’t necessarily want to be CEOs, just little different roles. People go back to that comfort zone. Someone’s a good fundraiser, for example. Outside, it looks like they’re a huge success but then what they’re doing is talking to more investors and keeping those relationships fresh. They’re not getting to the business building part of it.

The success metric for the first 4 or 5 years of a company externally is how much money you can raise. Just because you raise the money doesn’t mean it’s going to be successful. In counter, you have a lot of people who don’t want to have those conversations. They feel bad about asking for money and stuff like that but they have to, so they take the first offer they get or get the process done as quickly as possible.

To pivot on the incentives question a little bit, you want to think about that when you’re considering other people’s seats on the other side of the table. I’ll give you a few examples of this. It’s huge for Angel investors. A lot of the classic Angel investors, and part of why I wanted to get started so early in my career, is someone who’s been there, done that and who’s been in the business or industry for a long time. They have a lot of capital and are willing to do it. They have been a CEO and founder.

It’s hard for that person to give someone money, not give them advice, and tell them how to operate. For founders, it’s a tough zone where if someone gives you $1 million, you want it and they tell you to do something, you feel like you have to do it. You feel like you have to take that advice. I’m not the biggest investor in any company. If I’m your biggest investor, you have problems.

Skin In The Game And Aligning Incentives

Part of the reason why I invest, even if it’s small amounts, and that’s a lot of Halo Labs and syndicates I run, is we do a couple of thousands of dollars. The good thing about that is it gets the incentives right. You got skin in the game. It’s easy to give advice when you don’t have any skin in the game. Something that founders run into trouble with is they’ll start taking advice from people who are not their investors and who don’t have any real skin in the game.

To get down to the incentives on that, it’s like, “I’m incentivized to give you crazy advice. If it works, you think I’m a genius. if it doesn’t, I don’t have any of the consequences.” Part of the reason why I like to invest and put skin in the game, even if it’s tying up capital for years, is because I want to be coming from a place where my incentives are aligned and I’m able to do that. It can be very helpful for teams.

Part of the beauty of me working at startups, being an operator, and having worked with a lot of companies is sometimes founders will call me because they know I have skin in the game and I’m incentivized. They don’t always want to ask a VC who’s given them millions of dollars simple questions or questions or bring them challenges that they don’t know how to solve.

What you want to do is use incentives as a way to understand where’s that person coming from and how I can make sure I know what I’m doing. When it comes to investors, at the end of the day, even the large ones, they want it to be successful. If you do something different than their advice but it’s still successful, they’re not going to be saying, “We don’t want that money. You didn’t listen to what we said. We won’t be taking it.”

The reverse is not true. If you do what an investor says, they’re not going to be like, “I gave you bad advice. No worries about that.” I view incentives as a way to decode people’s decision-making. Understand what seat they have at the table. I always try to put that in people’s minds. Where is this person coming from? Take a minute to understand that before you start making assumptions.

The athlete in me, I wish everything was incentive and performance-based. When I’m confident in what I do, I know my upside is bigger because if I perform, I’ll get that. If I got ten sacks, it’s in my contract, and I hit that million-dollar bonus. I wish everything that we did was performance-based because I’m used to working out of those standpoints. You think that everybody is comfortable.

For example, I put people in a sponsorship position. You’re talking about giving them a percentage of the sales or a big upside. We have some people saying, “No, I’d rather take the monthly.” That is a red flag for me. You have an opportunity to make six figures more than what you’re getting paid monthly. You rather take that as opposed to the upside or the bigger percentage? If you go out and perform, this is a 10X. You perform and do what you think you can do. I tend to stay away from people who are the other way when they’re looking for a guarantee and monthly. They’re not looking for that upside.

That makes a ton of sense. You want to work with like-minded people and align the incentives. If that’s how someone wants to operate, that may work for them. If that’s how they built their business, you’ve got to respect it, but you don’t have to work with them. You want to have people who are like-minded and want to view things that way. For some people, you never know what their personal situations are and where their business is. It’s okay. That’s important to you. One of the important criteria is I want that.

I like skin in the game. To me, that is a big part of risk management. Who is giving the advice? Whose perspective is it? If they don’t have any skin in the game, it’s not worth it. Everyone knows that when you have skin in the game, you work harder. There’s less BS, lying, positioning, and nonsense when you have that incentive and you’re part of a production. Everyone gets paid if it works. No one gets paid if it doesn’t. You don’t have to worry about someone being like, “My check already came. I’ll get around to it.” They’re grinding with you. When you’re building stuff from scratch, you need people who are going to grind. That’s the reality of it.

Lightning Round Q&A

In the interest of time, we’re going to do a lightning round where we’re going to ask you a couple of questions. You got 30 seconds or maybe 1 minute max to answer each one.

I’m concise with my answers, as you can tell, Zack, so that’s going to be no problem for me.

What’s the number one thing to do to stay motivated when stuff gets tough?

That comes down to the before. You have to pursue things you’re passionate about is what I would say. You’ve got to go for it. If you get too overwhelmed and your motivation is questioned, my very basic advice is to walk or hike. Go get away from everyone else. Tune out the noise, get some space, and have that honest conversation. Am I trying to do this? If your motivation is lacking because you don’t want to do it, you have to listen to that sometimes. It’s not to just keep pounding your head. You pursue things you’re passionate about. If you ever are not passionate about something, chances are you’re better off going and finding something that you are.

Next question. What’s one thing you’re thinking about that nobody else is?

For me, it’s legacy infrastructure. I got so involved in this Lake Tahoe stuff with what’s happening up there and telcos. There’s an incredible amount of creation that’s happened through our society over the last century as we’ve connected the world. Something we’re not thinking about is all the stuff we’re no longer going to be using. What’s going to happen with all these telephone lines when we’re all on cell phones and off satellites?

I would say trash and pollution in general, I’m pretty focused on that and do it in a healthy way, not just being like, “It’s nasty and horrible,” and sue the bejesus out of everyone. That’s not a productive way to work on anything. How do we come together as a society and approach some of the burdens of the past that we all have to deal with without pointing fingers at each other?

Just so people know, what you did with Lake Tahoe is pretty incredible. Briefly tell everybody what you did there.

There were 6 miles of old decommissioned lead cable that hadn’t been used since the 1980s. This was something that the neighborhood and community knew about. We were writing letters for years. There were lawsuits associated with it. The cables were supposed to come out. There was a court order to do it. There was an agreement. Lots of nonsense took a long time.

Wall Street Journal wrote a big article. There were a lot of different reasons and noises. AT&T ended up not doing the project. What I did was get together with some friends and said, “If they don’t want to do it, we’ll do it.” We started a company, brought people together, got a petition, started working with the agencies, and said, “We’ve got no problem with AT&T and what happened in the past. No one who was alive chose to do this, but it’s a problem now, so we’re going to deal with it head-on.”

We rallied people together and ended up getting our first permit from the US Army Corps of Engineers in September 2024. Within a week, AT&T announced their new plans to remove it themselves. It’s already out. We got the lead out. We had over 100,000 pounds of lead cable out of Lake Tahoe in November 2024. It’s a pretty huge win for the community.

That was something to talk about, the failure and the challenge. That was something at the beginning where people told me, “Don’t get involved with that. It’s too risky. It’ll never happen. There’s no way. They don’t have to do it.” All these reasons why not, but for me, at the end of the day, it’s like, “I don’t know anything about all this. I don’t know the history of environmental or telecom. I don’t know all this other stuff but I do know that we don’t want lead in Lake Tahoe. I’m going to work to get it out.” Now, it’s out.

One thing that you hit on that is important is when you’re given an opportunity, there’s also a challenge there. A lot of people look for all the reasons it won’t work. I go back to this analogy that I learned many years ago. I learned how to ride a motorcycle. They teach you that when you’re on a motorcycle, wherever you look is where you go. It’s different than a car. When you’re on a motorcycle, you’re directionally going to go wherever your vision is pointed.

Let’s say you’re riding on the road and there are obstacles in front of you. If you look at those obstacles and anchor on those obstacles, you’re going to go right into that. You’re going to crash into those obstacles. What great people do and that you did with this Lake Tahoe project is you didn’t think about all the obstacles. You look for a path forward. Instead of looking at the rock in the road and going right into it, you look, “What’s the way that I can get around that?” That’s what you did. You were able to do something that nobody else has ever done.

Do not make assumptions. The big one for me is everyone is making assumptions, pointing fingers, and looking at the media and lawsuits but not actually going in, doing the work, and opening up the hood. Something that we learned at NYU and risk management is you open up the hood and check it out. You see what’s happened. You bring a fresh perspective to it and then say, “What are we trying to achieve? Does all this other stuff matter? Is there a way to get through it?”

What’s one habit or mindset shift that does change your life for the better?

There are a lot of different directions I can go. I’ll plug yoga. I was over 300 pounds at one point. I was an O lineman. I was going to gyms and throwing on Metallica, Rage Against The Machine and some other stuff. I was lifting weights. I was all about that. I had a back injury. That was not working and I ended up getting in the yoga game and I haven’t looked back. That’s something I’m doing every day.

It’s been a complete lifestyle change. If you would have said growing up, “That’s the yoga guy,” no one would have ever believed it. I love that. That mentality made me a little less too crazy about stuff. I was taking that beat and breath. Getting through injury is always tough for big dudes. I was less angry about stuff that didn’t bother me as much. That’s been a huge one for me.

It’s funny. Offensive linemen go here and get smaller when they don’t. All the guys who play are over 300 pounds. They trim down and play models now. They’re 230 pounds and they slam and everything else. That weight is gone. Zack, I want to ask something for me because it was important. One of the things I did was start my week on Sundays. I treated my Sundays like Mondays. It has completely changed everything.

Normally, people would sit around. I still watch football. I got the commentator broadcast stuff so I’ve got to go into studio sometime. We’ll hop in these podcasts and know what’s going on around the NFL. I watch the games. I’ll go get my workout in early. I start preparing. I get everything ready on Sunday. By the time Monday hits, I’m already in full swing of things.

Several years ago, I started to prepare on Sunday instead of sitting around getting ready. I get up at 5:00 on Monday and get ready to go on. I started getting up and treating my Sunday like Monday. By the time Monday and Tuesday hit, I’m already in the swing of things and not playing catch up. For me, it was starting my week on Sundays.

Once you’re trying to make things happen, you end up working on the weekends because that’s when other people aren’t working. That’s when there’s the opportunity and you’re not going to be getting bothered by emails and stuff like that. You’re pursuing something you’re passionate about. It’s easy to get your week started on Sunday when you’re working on stuff you want to make happen.

One of those signals that you’re on the right path is when it’s like, “This isn’t work. This is fun.” I got kids. For me, work is the break. “I can’t wait to work. I get to spend two hours in front of my computer. Are you kidding me?” You want to be working on stuff that feels like fun. That’s a big secret to success. If you’re able to make a livelihood and make work out of stuff that feels like you’re enjoying, that’s a big win.

The other thing I’d add to that is it’s what you do when people aren’t watching that makes you successful. It’s what Shawne’s doing at 6:00 AM on a Sunday when other people are sleeping until 10:00. It’s what I’m doing on holidays when people are like, “I’m out for a couple of days.” I can get in 40 hours of work in 3 days and I’ll be a whole week ahead of them when they come back. That’s why I always play from behind.

It compounds. If you’re able to carve that time out, you can pursue different things. A lot of the stuff I’m doing on the side, that Tahoe stuff, is nights and weekends. That’s not during the day. With the Angel investing, I’m looking at stuff at night. That’s what it takes. If you want to go to that next level, you have to carve that time out. That’s why you guys are both in a position where you’re working on stuff you love doing and you’re trying to make it happen. One of my big definitions of success is when I wake up in the morning, am I excited about what I get to make happen that day? If I don’t feel that way, I have to figure some stuff out. When I go to bed at night, am I pumped up for tomorrow? If you get those two dynamics going, you can get a lot of stuff done.

Evan, it’s been great having you on. I always learn something when I’m talking to you. I appreciate you coming on and sharing a lot of your insights with us.

I appreciate it. Thanks, Evan.

Thanks, guys. I appreciate it. Have a good one.

See you soon.

You got it.

Important Links

• Zack Ellison on LinkedIn
• Zack Ellison on Instagram
• The 7 in 7 Show with Zack Ellison (podcast)
• Applied Real Intelligence (A.R.I.) website
• Shawne Merriman on LinkedIn
• Shawne Merriman on Instagram
• Lights Out Sports TV website
• Lights Out Xtreme Fighting website
• Evan Dreyer on LinkedIn
• Tola on LinkedIn
• Halo Labs
• Tahoe Lead
• BAYKEEPER

About Evan Dreyer

Evan Dreyer is an executive, investor, operator, and community leader. He’s currently the Head of Risk at Tola, a VC-backed payments company for small businesses, where he oversees all platform activity and built the supply chain financing offering. Evan is co-founder and Managing Partner of Halo Labs, an angel syndicate focused on the Y Combinator ecosystem. He’s backed 50+ startups and early stage funds across industries around the globe.

Passionate about community impact and environmental issues, Evan has served on several nonprofit boards, including currently at San Francisco Baykeeper. He started the Tahoe Lead Removal Project, which successfully advocated for the removal of over six miles of inactive lead cables from Lake Tahoe.

Evan spent the first 12 years of his career at Credit Suisse, with roles across Capital Markets, M&A, Strategy, Trading and Risk Management. From new issue origination to hostile takeover defense, strategic business planning, trading oversight and implementing automated solutions, he has extensive front to back experience at this global financial institution. He holds a MSc in Risk Management from NYU Stern and a B.A. in Economics from the University of Chicago, where he played football.