Neil Patel

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Andrew Endicott’s journey is a testament to the multifaceted nature of the fintech landscape. From the intricacies of deal-making to the art of balancing innovation and experience, his insights offer a roadmap for aspiring entrepreneurs navigating the complex terrain of finance and technology.

His latest venture fund, Gilgamesh Ventures, has attracted funding from top-tier investors like Clocktower Technology Ventures, Picus Capital, Blank Ventures, and Flyover Capital.

In this episode, you will learn:

  • A journey showcasing the multifaceted nature of fintech, offering insights for aspiring entrepreneurs navigating finance and technology’s complex terrain.
  • From weathering the financial crisis to mastering the art of deal-making, career evolution provides a roadmap for strategic transitions in the finance and fintech sectors.
  • Petal revolutionizes credit accessibility through cash flow underwriting, addressing challenges faced by those traditionally underserved by credit scoring systems.
  • The shift from a corporate job to entrepreneurship highlights the grit required for meaningful ventures, emphasizing the intrinsic drive entrepreneurs possess.
  • Fundraising complexities in fintech emphasize understanding the desired scale and proof points for equity and debt, resulting in Petal raising approximately $0.5B in debt capacity and $350M in equity.
  • Balancing innovation with industry experience is a perpetual challenge in fintech, emphasizing the importance of harmonious team dynamics for sustained success.
  • Board dynamics play a pivotal role in a company’s trajectory, with a focus on tailoring board composition to the company’s stage and avoiding pitfalls associated with inexperienced members.


For a winning deck, see the commentary on a pitch deck from an Uber competitor that has raised over $400M (see it here). 

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About Andrew Endicott:

Andrew Endicott is the CFO, President, and Co-Founder of Petal. Prior to co-founding Petal, Andrew was an investment banker at Lazard and focused on buy-side and sell-side acquisitions involving consumer-facing companies and non-bank lenders.

Prior to that, Andrew practiced corporate law at Willkie Farr & Gallagher LLP, where he focused on public and private M&A, along with securities offerings, including IPOs, equity and debt offerings, and other transactions.

Andrew holds a J.D. from Harvard Law School as well as a B.S.B.A. from the University of Arkansas and is a periodic lecturer on strategic transactions at the Walton College of Business at the University of Arkansas, where he is also a member of the Dean’s Alumni Advisory Council.

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Connect with Andrew Endicott:

Read the Full Transcription of the Interview:

Alejandro Cremades: All righty hello everyone and welcome to the deal maker show. So today. We have a really amazing founder. You know a founder that they has really experienced both sides of the table. You know the founder side. The investor side his company. Actually they they the the last one that he built has raised. A lot of money you know between equity and debt I mean close to a billion. You know if you put both you know in in one go so it’s really remarkable. We’re going to be learning today around really finding product market fit around fintech building a team to win fintech fundraising in fintech and also how to think about. Investments when it comes to having a global mindset and perspective. So again, incredible episode that we have ahead of us but without farther ado let’s welcome our guests today Andrew Drew andic car welcome to the show.

Andrew Endicott: Hey I hunter how are you doing.

Alejandro Cremades: So originally born in Mississippi so give us a walk through memory lane. How was life growing up.

Andrew Endicott: Yeah, it was ah was a lot of fun. So I’m from the the southern us I I was born in Mississippi Grew up in Arkansas very much in the south and went to went to college down here I was a razor back and and ah in school but graduated. Kind of into the financial crisis like a lot of people who who went to to school and I did and graduated from college and and um, you know I’d studied finance and accounting and kind of planned for a career on wall street which which was ah harder to come by in 2008 and 2009 so it was a good. Not as good a time to get a job but a great time to to go to school so I I left and graduated college went to Harvard law school spent a bunch of money in 3 years getting a law degree but but also met a lot of wonderful people I was there to in and.

Alejandro Cremades: And why law school out of out of all things you know for someone that studied finance and accounting and you know obviously now very much into business and and startups law school where where does that come from that interest.

Andrew Endicott: Yeah to be clear. It’s it didn’t come from me liking to argue I it’s it’s a that’s a reputation of lawyers that I that I I kind of wish we didn’t have um I like I like being able to Zoom out and think about how things. Really work thinking about things in systems thinking about things holistically I think I think being being a lawyer going to law school um helps you think about public public policy and things like that that that are that are you know, maybe not immediately applicable to to starting a company or investing in companies. But. But ah it helps you think I think in a good way.

Alejandro Cremades: Now it did it did serve you because obviously you ended up going into um, working for a law firm after law school and you were there in the corporate department. So obviously when you’re getting to see this deal making things that don’t work deals that fall off you know through the cracks whatever happens.

Andrew Endicott: Is.

Andrew Endicott: Um, that is.

Alejandro Cremades: What did you learn from on the deal making side. You know when it comes to because obviously people are like yeah let’s do a deal and then when you go really into the details. You know that’s where deals fall apart. So what did you see? What were some of the patterns that you encounter while you were experienced there first.

Andrew Endicott: yeah yeah I think that there there was a lot of them I think the one of the things is that you know I was mainly I began my career almost entirely in m and a which the m and a setting is a little bit different than the kind of the the investing. Setting to to be much more confrontational much more the the terms you’re trying to figure out are much broader because it’s it’s kind of final for the most part. Um, so that’s that’s some context around it. But I think 1 thing when you start an m and a transaction. It’s very hard to tell. How it’s going to end. Um, everybody can be very excited about a deal. The price can seem like it’s ah it’s a great deal for both sides and deals can still fall apart relatively late into things just because they’re so complicated. Um, and so you never quite know when something is going to finish. Um, or how it’s going to end I think that was that was an important thing around around ah dealmaking I think another one is the personalities really matter. Um, the the ah the people the main decision makers you have around the table. They often have very large egos they they? Um, they have a lot of pressure. Um, they have a lot of things they’re optimizing for and those things inevitably come into conflict. Um and how they resolve those conflicts. Um, if they do at all um has a lot of impact on the outcome of the deal and I think one of the other things I learned is ah you know it’s it’s Boon Pickens

Andrew Endicott: Ah, it’s a quote he he he has, but but um, if if you want to a deal Real Bad. You’ll get a real bad Deal. So having the ability to walk away is incredibly important. Um, and sometimes you need to to kind of illustrate that willingness to walk Away. Ah, particularly in name and a setting but I think in all all deal making it’s It’s somewhat important to to to kind of be able to have a backbone about what you’re agreeing with and a lot of times that comes through through just saying no and so that’s I think I learned those things. Ah, both as a lawyer and and as ah as an investment banker and throughout the rest of my career. Those things have been pretty.

Alejandro Cremades: And I wanted to ask you that too I mean obviously you’ve seen deal making from every side of the angle now of the people that are going to be sitting at the table. Um, now the next chapter in your career was investment Banking. You did that at Lasar you know, really reputable investment Bank. So How do you think that that. Dealmaking approach. What? how? what? What did you see that you couldn’t believe that that was the case you know, Obviously when you were looking at it from the from the lawyer’s side now all of a sudden you are moving. You know, ah to another side of the table. What were some of the aspects of the deal making that you were like. Wow! This is incredible.

Andrew Endicott: Yeah I think the the when you go from being a lawyer to being an investment banker. Um, you’re you’re a little closer to the the core activity you’re you’re really there when price is being set when you’re you’re bringing to the table the buyers or or the sellers. Um. Seller you’re usually not to not multiple sellers in this time. Um, and so you you understand a little bit more kind of why those people are there than you do as a lawyer. Um I think one of the things that that I found fascinating as a banker is how fast. Some things can really move and and a good investment banker or really a good good kind of a good seller of anything you’re doing um you do prioritize speed. Um and you because speed allows you to to get good prices to get good terms. They create auction. Ah, dynamics for for sellers now it depends on the market conditions. You know if you look right now. Um, you can’t you can’t always create speed if you’re a seller. Um, when when when you’re in when you’re in a down market. It’s more of a buyer’s market. Um, and in the the balance of power shifts. From sellers to buyers and so that’s where we are today and times like that if you try and speed a process along or you try and speed speed a transaction too quickly. You’re actually more likely to to blow it up the the transaction just won’t occur so there’s a lot of art and intuition.

Andrew Endicott: Um, at at its core to to run a to to manage a transaction whether you’re a banker or you’re the or either the company or the thing being sold itself. Um, there’s there’s more art than science and the pace and the speed often can have a pretty dramatic impact on the actual outcome. Ah, so that that was that was another another thing and I think the biggest thing you learn as a banker is that that valuations while there is some science to them. There’s a lot of art. Um, and and um, you know what something is worth very much depends on who is who is looking at it. There’s much of the. The I the beholder effect beautyautiess in the eye beholder valuation is two. Um and you know a 1 1 thing can mean many different things to many different people. Um, and so it’s not just a purely mathematical exercise. Um, things valuations are very much relative to who you are. um and so I learned that um and I think I learned a tremendous number of things that eventually be important in my career I you know the the being today. All of my time being in fintech. Um, you know I was working not exclusively but primarily with companies and the. Lending and and and kind of Nonbank Financial Institution world at at Losard. So I learned a lot about that as well.

Alejandro Cremades: So ah, what point does the you know it’s interesting because you’re getting closer and closer to the people that are making the decision all of a sudden in deal. Finally, you are like on the founder seat. So how does the experience or thed petal come come knocking. How did that happen. Okay.

Andrew Endicott: Yeah, it came from ah of a variety of sources I think you know that’s that’s the reality of kind of how how businesses really come into being I think usually there’s there’s you know, unless you’re a single founder. Um I think it’s a little simpler than but but it tends to be more a little bit more of a mosaic. Ah, than just a a bright kind of line of inspiration. But but um, you know I think over the the period of time that I graduated from law school ah to starting pedal and and um I had ah had a number of friends that that ah that had kind of peculiar issues with getting access to credit. Um, yeah, my my my current you know, kind of partner with with Gilgamesh Miguel had had this as well and had to you get a secured card to to be able to get access to credit coming from outside the us and my you know the with my my my cofounder Jason with with pedal had had seen the same thing. Um, and so you know this is not It’s not a secret that that there are significant difficulties getting access to credit if you’re younger if you’re from another country if you’re a divorce say if you’re a veteran um nobody believes that credit scoring works perfectly in the United States it’s pretty it’s it’s it’s very very rigid. Um, how you build a credit history. It depends on relatively few activities. Um, and so you know the the the but it was primarily personal relationships and seeing.

Andrew Endicott: You know issues that people had had building credit and getting access to credit. Ah, that really was the the spark and then also using the the the knowledge that I’d accumulated um through the years as as ah as a banker working with um, you know, kind of nontraditional lenders. People that are lending money to folks that that haven’t had a lot of access to credit and also as when I was a lawyer I worked with some some companies some fintech businesses including yodeli that were that we’re doing some interesting things around providing data for underwriting that were really interesting so it was a lot of things and. And um, you know I think but I think the at the end of day Jason and I being both very interested and in this segment of the economy was you know, just as important as anything else. This is something this is the kind of company. We wanted to build um and that that was a big part of it as well.

Alejandro Cremades: So then how how did the whole idea of obviously experienc this issue is experiencing this issue seeing friends that were experiencing this too. How does it go from just having a chat you know with with with a friend to all of a sudden you’re like let’s give the notice here.

Andrew Endicott: Ah, yeah.

Alejandro Cremades: Let’s take action because I mean here you are a lawyer you know, very corporate, a courier a law firm then an investment bank a large investment bank I mean going from all of that you know the kuchin the cushion you know job and the 9 to 5 and the nice paycheck to all of a sudden you’re like. Doing your own photocopies and a you know, no more assistants and nothing like that I’m sure it was quite humbling for you. So.

Andrew Endicott: Yeah, well the the life of a corporate lawyer and investment banker is is far from 9 to 5 or cushy in my experience what it’s worth. but but um yeah I mean I think that you talk to any founder of a company I think that there is a.

Alejandro Cremades: Ah, yeah, so.

Andrew Endicott: There’s a common thread that you have an idea you have a a um you know you you see something ah that simply compels you to build it. Um, and yeah, that was very much true for me building pedal I think by the cofounders that was also true. Um. But also I think for Gilgamesh and and starting the investment fund um was true too. The I think you the ah people who become entrepreneurs. Um, maybe not across the board. But for the most part they see something that that kind of the the they they don’t have the ability to not. Um, and that that was the experience for me. It wasn’t really an option ah to to stay at lazard and to continue doing working for other people and and doing these things you know I was learning a lot but that the the ability to build something new and to to kind of determine my own destiny was really really. Important. Um, and I think that that’s that’s at the end of the day. That’s what did it? It wasn’t it wasn’t like a a rational calculation because I think if you look at the stats if you look at the the probabilities if you rationally calculate it you probably shouldn’t start a company. He published you probably should stick to to your your your your your job where you’re making good money rather than take tremendous amounts of risk to build something that doesn’t exist.

Alejandro Cremades: That’s right.

Alejandro Cremades: Absolutely so for the people that are listening to get it when ended up being the business model of pedal.

Andrew Endicott: Yeah, so pedal is a is a um is a credit card company in the fintech space where we we provide access to credit and and a credit card to people who have limited credit history and we use we call cash flow underwriting. Ah, which is a where we’re we’re getting access to bank account data in addition to bureau data and all the other traditional information and we use that information to underwrite credit and to to approve people for a credit card that would otherwise have difficulty getting one. Um and. The the product itself works just like any other credit card. it’s it’s it um you know it’s but it’s a visa branded branded card where you have ah you have a credit limit and you use it and you know pay back at ah at on a certain schedule the amount that you borrow. Um, and we’ve we’ve developed a number of partnerships over the years with lenders and with issuer banks and and payment processors and and other other important you know either intermediaries or partners to to make the product function. Um. And you know the ultimate goal is to to take a population. That’s that’s you know anywhere between 40 and 100000000 people depending on how you you you arrive at the numbers um to help that population get access to to to credit to make their lives more.

Andrew Endicott: More livable and and a you know to to to give them access to the the same tools that that the affluent and everyone else has always had um and that’s really the goal of the company but we we make money when when we partner with when we when we have customers that use the product responsibility responsibly and pay us back. Um, and you know we grow the number of customers. Um under the platform.

Alejandro Cremades: Ah, what point did you guys realize that you had product Market fit with pedal.

Andrew Endicott: Yeah, but Product Market fit in fintech and and I’ll talk a little bit about pedal. But also you know I think more broadly. Um you know I think that the the idea of product Market fit can be a little tricky um in in specific parts of and of fintech. Not all of it. But particularly any time that you’re taking risk.. There’s There’s always a little bit of a challenge of knowing whether you have it. Um, and so let let me give you an example when when you’re lending money. Um, you know you? It’s very easy to find people who who will take money from you who will borrow the money. Um, and if you look at the traditional metrics of product Market Fit Ah, which are you know, kind of cost of acquisition and and kind of ability to put something out there and grow and feel the market pulling you um those kind of traditional ideas around product Market fit.

Alejandro Cremades: Me.

Andrew Endicott: Um, they don’t always work so well with credit because you can you can be offering a product that the the market really demands but that is very destructive to you from a Unity Economics Standpoint so with pedal really the I think the the way that we we determine we had product market fit. There’s no obvious point. It happens but it’s where when you are you are you know, kind of growing the cohorts um of the program of of the the platform and acquiring customers. Um at a at a cost of acquisition. That’s that’s reasonable on that fits within the. Kind of the the framework of what what you can do to be profitable and you’re you’re charging a rate of rate of kind of a cost of of capital or an interest rate and the things you do to make money in ah in a credit card that’s market. Um, and you’re not seeing. Excessive indications of of um, kind of customer weakness. So you you have to make sure. Not only do people want it are you able to find those customers affordably. Um, it is the product flying off the shelves kind of in ah in a qualitative sense but you also have to check to make sure. The customer that’s using your product is the type that’s going to have the right relationship with you. Um, and this is you know this? This is true for a pedal but this is also true. Ah for other asset classes like ah insurance and sure tech you’re underwriting a customer you’re you’re really taking risk.

Andrew Endicott: Um, and whether that customer is going to have the right behavior that you want and and you know I think for for these kinds of businesses. It’s it’s more iterative over over a period lasting years for you to to really be sure and you’re never It’s never perfect because you’re always kind of straddling this line of. Taking too much or too little risk. Um, but you you you determine it in the early days by by seeing that everything kind of lines up with how it should be It’s a little more prescriptive um in how you you you figure it out both in lending and outside lending infantile.

Alejandro Cremades: And obviously you know for a cheing product market fit. You need a great team. What about building teams in fintech. You know whether it was with petal and and other stuff that you’ve seen like how how how should people you know how they should think about building a team when it comes to fintech.

Andrew Endicott: Yeah, the the I think I think this is true of any business. Um in a complex industry which I consider finance to be complex. But it’s also probably true if you’re operating in healthcare um, or you know, maybe something from anything pharmaceutical. Things like that where there’s it’s more than you know produce a product and sell it. You have regulatory considerations. You have kind of in the health tech you have you know, kind of the health of the customer and kind of all the the variety of considerations that come in with that and privacy issues. Um, but in fintech um there’s a perpetual challenge. Ah, which we had ah at a pedal for sure. But every fintech company I think has where you you struggle to achieve the right balance of innovation on one end of doing things differently because if you completely copy what chase does you’re not going to do anything special. Um, or if you if you’re an insurance company if you completely copy what? What a Geico does. You’re not going to do anything special. You’re also going to fail because you’re not Geico um, so you have to innovate but in the other at the same time you you have to also kind of respect the laws of the the category if you will. Ah, respect the the forces at work. Um, and so you know to do that you you have to bring in people that are experienced um and so in in many fintech that means hiring people that have worked at banks or have worked in in the payments industry and things like that.

Andrew Endicott: Um, in the world of insurance. It means hiring somebody’s worked Insurance Company. Um, and and there’s always a huge tension in getting the people that that have experience to work well with the people who are more on the innovative side. Um, and so that’s something that. Um I think is always going to be iterative when you when you start a company. Um and you’re scaling it in particular, it’s It’s not so much an issue early on it’s more.. It’s more of an issue kind of as you grow. Um that you you need to get these people to work together. Um, because they the the the innovators need the experience folks. Whether they know it or not in the experience. Folks need the innovators whether they know it or not and the company needs them both um and so you know it’s important to have an environment where people respect each other you know there’s a lot of Mutual Respect. It’s important to give people the time to to to kind of talk. About their perspective. You know when you when you have multiple functions doing things. Sometimes it’s important to to have people sit in room and fight things out. Um, that’s something that I think is underappreciated about managing a culture and running a company is you? you need to sometimes let conflicts really. Resolve themselves directly conflicts is not always bad. A lot of times. It’s actually quite good to to work through a conflict in a in a in a direct setting and let people say what they really mean because the other person often won’t understand it until they have that opportunity.

Andrew Endicott: Um, and and most importantly, a lot of times people simply will be incompatible. Um with the organization you’re building sometimes you will have somebody who you know has has come from a pure pure software role for their you know for the the entirety of their career. And they don’t believe they just they just completely reject what somebody who has a full understanding of bank regulation um has to say about how to build a product that person’s not going to be compatible with the Organization. You’re building and similarly you’ll have somebody who has worked in in an industry for a long time. And has very set and established ways of seeing how to build a business and they’re not flexible and that person is going to be incompatible with the culture you need to create um and as a leader you have to know the difference between when when there’s the right amount of conflict where people are learning. And when you you’ve really reached an impasse um and and making those decisions is very hard. Um, but it’s but it’s really important.

Alejandro Cremades: And when it comes to a fundraising obviously fintech companies their capital intensive. Ah you know for pro you guys have raised quite a bit. You guys have raised a I believe it’s half a billion on the deb side and then also 400000000 on the equity side. So talk to us about raisingcing capital in. In the fintech space.

Andrew Endicott: Yeah, the the in in fintech. Um, it’s it’s a big category. Um, so some fintech companies are more like pure software. You’ve got saas businesses that that are going to really resemble more. How how sa aspects business functions and then you’ve got ah businesses that have more of a balance sheet. Um and that are that are going to be valued and grow more kind of on the trajectory of of kind of institutions that more resemble that what what I would say is that I think. Um, when you’re fundraising in fintech and when you’re building a capital structure in fintech. First of all, you need to understand what you you need to look like at scale. Um, and so um, you know for a software company. That’s relatively easy. But if you’re building a business that’s going to have a balance sheet that’s going to require debt capital. Um, or require. Um, you know, kind of reinsurance and things like this on the on the other side of the equation. Um, you need to to understand before you start um, kind of how those things are going to evolve. Um, so that’s that’s the first thing. Um and you you need to understand. The the proof points that you need to generate. Um, along the way for the different types of capital. You need to raise so typically when you when you start a fintech company kind of regardless of what the type of business is the first thing you’re going to do is raise equity capital um, that’s something that you’re going to need to do you raise a seed or a pre-seed round.

Andrew Endicott: Um, you know that’s that’s relatively basic and it’s like the rest of the world of startups that that’s where you begin? Um, but often in fintech that’s where the similarity is kind of stop. Um, for many businesses you then need to find a way to you know, kind of if you’re in the the lending world. You need to be able to find a way to access your inventory which is really money you need to find a way to access that money at a cost of Capital. That’s not going to completely destroy your return and Equity. It’s not going to just not going to cause dilution. Um that the cripples you know. Not only the investor’s rate of return but also your rate of return as a founder because the end of the day you you pay? um you pay for for dilution. You pay to raise raise Equity Capital and Equity Capital is the most expensive capital that a business can raise. Um so you need to figure out kind of. How you can access that capital and when you need to access that capital along the journey ah to to be successful. Um, and so typically you’ll have a seed round. You’ll have a preseen round um and for for a lining business or or other businesses that have more of a balance sheet component relatively soon after that you often need to start building. Relationships ah with with um with asset-based lenders and and with with um with other types of institutions they can provide you capital that you either loan out or do other other things with so that you you don’t have to raise so much equity. Um, and so that’s that’s that’s.

Andrew Endicott: Another thing you have to do is you have to think about kind of when to start doing this but typically it starts earlier than you would think um and also it has critical implications for how you what the milestones that you’re you’re wanting to to to aim for as a company. Um and what what those types of investors care about. So um, equity investors you know are much more much more focused on growth. Um than other types of investors particularly venture capital investors are much more focused on growth. Um, even today they’re more focused on growth than other types of investors debt investors are much more worried about security. They’re worried about getting their money back. Um, in one piece and so you know the when you’re when you’re raising a complex debt capital structure where you’re going to have to raise debt you’re going to have to raise equity you have to keep in mind um that you have to make both sides. Happy. Um because the equation doesn’t work without 1 or the other. Um. To to build a business with with ah with a balance sheet that’s in the lending space. Um, you you have to have equity because the the debt will never come unless you have equity capital to to kind of support it and without debt capital the business will never make sense because you will face such an extraordinary amount of dilution. Ah, that it that it destroys any rate of return and either that you or your your early round investors will ever ever ah see. Um and so I think it’s it’s important to understand the types of capital and to be able to incorporate into your plan for how you’re going to scale the business.

Andrew Endicott: How you can you know reach the kpis reach the milestones that those different sources of capital are going to require and all this boils down into why building in fintech is often very hard because the you you there’s more considerations. Um. You know, simply around fundraising if nothing else, but there’s more considerations for you to take into account because you have different types of investors for for most most startups for for company ecommerce or Ai or or anything like that. Um, it’s really simply about. You know, evolving from early stage investors to gros stage investors which is a complicated thing in and of itself. Um, you know you have to you have to understand kind of when the consideration shift from from proc market fit to growth and then ah to profitability when you reach where you reach growth stage investors. Um, but. When you layer on the the balance sheet component of a fintech company. Um, you got to think about profitability way earlier because not necessarily becoming profitable ah in the aggregate. But you know being able to show the right indications that you will be becomes important very very early on um and you’re just there’s just more parties that you’re trying to. Keep happy. Um, and I think one last thing is that when you when you if you’re in a business that that’s having to raise a complex capital structure. It’s really important to have people on your team. Um, who you need to have senior people on your team who understand every part.

Andrew Endicott: Of that capital structure and so for a lot of these business. You’ll need a you know Vp of capital markets or or some some role like that. Um that that ends up being pretty instrumental. Um and determining your strategy because they they kind of speak for the the capital market stakeholder that’s eventually going to be at your business.

Alejandro Cremades: Now obviously when when you get money it comes with responsibilities and especially on the equity side most likely there’s going to be a demand to secure a board seat from the people that are giving you the money and when it comes to boards you’ve learned quite a bit. You know you had the opportunity to of. Being a board member of Acorp Bank which is one of the fastest growing banks. So I guess when it comes to um board dynamics you know what would you say is the most important thing that founders that are listening should keep in mind. Okay.

Andrew Endicott: Yeah I think the the I said earlier in the m and a context that that personalities really matter. Um I think personalities really matter on boards because then in the day these are the the individuals on your board are people that that have enormous um influence over. You know, kind of what what you’re goingnna you know, kind of how your life’s Goingnna go and we we can. We can see this. You know today or when this podcast will come out but with everything happening with with openaii boards can can create issues and boards can can um you know their alignment with you is absolutely essential. Um, and on some level alignment often boils down to personality it boils down to how you communicate. Um, whether you have kind of interpersonal chemistry with with people um is is much more important than people give it credit for um and so I’m I’m very much of the view that it’s essential. Um, that you spend a lot of time with people who are going to be board members whether you’re a board member or you’re an entrepreneur. Whatever it is that you spend a lot of time together. Um to you know before you’re you’re really committing ah to to make that commitment with people. And this is true for investors as well as kind of independent board members need to do this too. Um, so I think personal interpersonal alignment is really critical. Um I’m a fan of of having you know relatively? um, relatively small boards.

Andrew Endicott: I Think you you need? Yeah, if nothing else you need to right size the board for where you are as a company now when a company goes public you you’re going to have a lot of people around the table. You’re going to have a bunch of independent Directors. You’re going to have you know the audit committee member and all all this kind of stuff but when you’re an early stage company. Um. You know for a while you probably shouldn’t have a board at all because it’s just it’s kind of it’s the wrong priority you need to focus on launching a product or whatever it is. You’re working on at that point before you get product Market fit. Um, but then even as you you start to to accumulate additional rounds of Capital. Um, it’s important that you. You know you have the voices in the room that you need and you don’t have more um and so you want people with knowledge you want people that that um are going to help you anticipate the the most significant issues that are going to come to you in the future. Typically those are going to be. Around kind of raising raising additional capital for the business um or achieving liquidity for the business. Those those are that’s that’s typically the biggest thing that a board member is going to be involved with with is helping you work through that. Um, and of course I think it’s helpful to have people who have operational experience. Ah, not not just because they’re going to be able to give you Advice. You know you as an entrepreneur you need to seek advice from a truly huge number of people because you’re dealing with so many issues that you’ve never dealt with and that maybe sometimes nobody else has ever dealt with um but the operating experience is really important because they can.

Andrew Endicott: They can understand where you are um and they they have a they have a they have a intuitive kind of grasp of what you’re trying to prioritize and why maybe you’re You’re not dealing with some issues. Um, yeah, there may be you may have an operational problem in one part of your business. It’s it’s simply not important. Um, to to your broader. You know, immediate strategic goals an operator somebody with operating experience is going to probably have a little more understanding that sometimes you let you let fires burn in a business whereas somebody who’s only dealt with very mature companies. Is not going to understand that. Um, So I think I think having having people who who’ve either been operators or have had experiences that give them. You know the the awareness of what operators deal with um is important and you you don’t want to have a bunch of people that that.

Andrew Endicott: Something you want to avoid is is you don’t really want individuals that that have that have not had a broad range of issue a broad range of experiences. Um, you need people that are pretty balanced and that have seen a lot of different things but and not saying they need to be. Super advanced in their career. You know that you can have people that that are in the middle stages their career. They’re gonna be great board members but they need to be flexible people that don’t get hung up on you know, something from 1 individual perspective. That’s this goingnna it’s going to divert your attention because at the end of the day. One of the biggest problems is. You got to take a board seriously when they ask you questions you got to answer them. Um, and you you it takes tremendous amount of time ah to to to to really faithfully answer the the questions and concerns they have and if you’re getting the wrong questions if you’re getting. If you’re having somebody paying attention is something that that the end of the day doesn’t matter. Um, it’s highly destructive to the the path of business and and your your time as an entrepreneur because at the day time is really your most valuable resource when you’re when you’re an operator when you’re a founder. Um. And you have to have people that are not going to not going to abuse your time or or waste it.

Alejandro Cremades: Now when it comes to um to you and and and obviously to the way that you decided for the next chapter I mean eventually you decided to go to the other side of the table and now you’re running gilgamesh ventures but how did that happen because here you are in an absolute Rocket Ship. You know. How do you decide? Hey, it’s time to turn page here.

Andrew Endicott: Yeah, so I’ve spent the you know much of my adult life I’ve been a pretty active investor going back to when I was in college I was pretty active. Um, you know I don’t have I don’t know my exact track record but but a pretty active yeah investor in public equities and. Spend a lot of my time and in in various things in college doing that. Um I took the cfa you know, pretty early before I went to law school took the cfa 2 before taking the bar which was probably the the craziest thing you’ve ever done doing that a month before the bar exam that was it was. Was ah I’m not sure i’ planned that one out that well, but but I’ve always had a I think part of this is interpersonal I’ve always I’ve always I think seen things like an investor I’ve always had a view that at at kind of the terminus in my career I would I would be an investor in an investment capacity. Um, at some point and so it’s something that I’ve always done and been focused on but but um, you know I think the naturally when you’re when you’re a founder. Um, you’re you’re close to the fundraising process. Um, you got a lot of curiosity about the other side. Um, so I think that’s something that everybody has. And it tends to be the case that founders tend to be pretty active investors. Um in other companies. That’s not something that’s unusual I think it’s a little less common today than it was a couple years ago but but um you know I was no different and relatively quickly after starting pedal. Um I started I became a pretty active investor myself.

Andrew Endicott: Ah, now. Granted I didn’t have that abundant of of of funds to do it. So it happened at a pretty small scale but but um, you know, almost immediately after you know so maybe not immediately. But after a couple years of pedal being up and going and us achieving success I started actively. Investing in people in my network and you know folks that I would meet in the fintech space. Um and mainly doing so with with ah a friend of mine that i’ve’ve’ve ah’ve I’ve known through you know through a variety of kind of acquaintances for a long time Miguel or maza. Um, who is my current partner. Um my cofounder with Gilgamesh he and I started investing together and that began organically it wasn’t something where we had some grand strategic plan ah to you know to to create an asset manager or anything like that. But we started investing together. Um, you know pretty early in the the journey with pedal and and it’s something that he and I both enjoyed and over time it took on a life of its own. Um and started investing outside the us. Yeah, really developing some expertise or maybe a reputation you know for investing in fintech companies. Ah, given you know his background and my background as ah, as ah as a fintech entrepreneur. Um and and it continued to take on a life of its own and then yeah ultimately became it became complicated enough that that ah became very clear that we needed to raise a fund if we were going to continue doing it and so we made that choice.

Andrew Endicott: Um, you know before the pandemic really really arrived um and and started investing our our first fund and it became very clear to me that this is really what I was built to do um I I liked being an operator and I’ve I have had the the good fortune to to do it. Um, and and have have have success in doing so but I think my my mind is is really that of an investor. Um, and so yeah, when we at the end of 2021. We raised a pretty large amount of capital that was a good time for me to step away and focus on on the fund. Um.

Alejandro Cremades: So.

Andrew Endicott: And which I did and you know today we’ve invested in 33 companies with Gilgamesh and and ahre we’re we’re investing out of our second fund at this point um and and um, you know investing you know, really in the future of finance and and how finance is going to work in the the next decade or 2 um, and the companies that are going to define that and we’re we’re doing that in the Us but we also were active investors in in Latin America and Canada um, and really try to bring a global lens to kind of fintech and and what the future of the category is going to be I mean we invest early so it’s. Something that that’s near and dear to me having been an entrepreneur. Um you know and helping other people. Um, you know to take that first step and build build the you know the huge businesses. The future.

Alejandro Cremades: So now. Obviously you’ve seen a lot. You know you have invested in in 30 plus companies as you were saying and and raised you know tens of millions to invest in them. You’ve also been a founder. You’ve you’ve seen everything. So if you had the opportunity to let hours to put you into a time machine. And I was to bring you back in time you know, perhaps that moment that you were in Las art and you were right about to give your notice. Okay and let’s say you’re able to have a chat with that younger Andrew and you can tell that younger Andrew 1 piece of a device for launching the business but would that be Ny. .

Andrew Endicott: Is.

Alejandro Cremades: You And what you know now.

Andrew Endicott: Yeah I think that the the thing for me is it’s important to understand what you have done. It’s important to use the knowledge that you’ve accumulated Um, you know in in the things that you’ve been. Been doing and the people you’ve been around um and the expertise that you’ve generated but the thing that will ultimately determine whether you’re successful is the intensity and and um, you know, kind of aggressiveness with which you. Continue developing. Um, you know a lot of people talk talk about things compounding over time and I I am one of these people that believes that learning compounds. Um, but that doesn’t just mean starting early, starting early is important. You know, starting saving money means that it compounds further. But it also means that you have to keep doing it. Um, and I I’m very I’m very ah convinced that um you know the expertise exists and people do know what they’re doing um but to to really know what you’re doing. You have to really approach. You know the important things that you do um with the the kind of the mind of a student um the the mind of someone that that’s not satisfied with their understanding with the the intellectual humility that that you don’t necessarily know everything um about.

Andrew Endicott: Kind of whatever thing you’re doing which is difficult because the when you’re in any position of importance. Be an investor founder. Whatever Executive Um, you’re getting paid because you know things and the you’re you’re there’s There’s a reaction that you need to exude. You know, confidence and certainty and all these things and those are important. You need to do those things. Um but simultaneous with that you have to question whether you actually know what you’re doing um and and find you know constantly tackle. You know those places where you you don’t have you know within yourself, You don’t have total confidence total total certainty um that you do know everything? um because at the end of the day I Also believe that there’s very few people that are true experts of what they’re what they do. There’s a lot of people that sound like experts. Um, and that that um, you know say the right things and and um can be very convincing and and all of that. But but to get to the point where you actually know things and you can you can actually see around corners and you can really make wise decisions that are not influenced by what’s popular or what’s. What what kind of everybody Else. Thinks is the right decision but but where you can really make the right decision requires a lot of time and effort in really deeply understanding what you’re doing um in trying to you know, avoid the thought that you you already know.

Andrew Endicott: Um I think and I think that’s the thing I would want to tell myself I try and think about it all the time now and I try to take the viewpoint that that you you should always be reading. You should always be learning um about what you’re doing because that your your success 10 years from now.

Andrew Endicott: Is not just what you’ve done to date or what you’re going to do. It’s what you’re going to learn um in the next 10 years.

Alejandro Cremades: Absolutely so Andrew for the people that are listening that will love to reach out. What is the best way for them to do so.

Andrew Endicott: Yeah I so like like so many folks I you know use social media and and ah not maybe not all of it. but but um also email my my emails Andrew at Um, hopefully that people can figure out how to spell it um little little googling can probably help but um, yeah, and then Linkedin I I tried my best to to ah to to be responsive to to things I see on Linkedin and and ah it’s helpful if it doesn’t look like ah an automated message. That’s what i. But I’d probably emphasize but but um, yeah I think that that’s the main ways and and yeah, we’re just if you know somebody who who’s connected to me have them nudge me tell tell me to respond ah that tends to help too.

Alejandro Cremades: Amazing, well easy enough. Well Andrew thank you so much for being on the dealmakerr show today. It has been an honor to have you with us.

Andrew Endicott: Yeah, absolutely honor for for me too and and um, um I’m really really honored, really flattered to be part of this and hopefully is so one of the things that I’ve said ends up being helpful to somebody. So thank you.


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