Be An Open Book

One of the values we had at Fundera was “Be An Open Book.” I used to tell people during new hire orientation that I loved this value because I am a lazy person. As a company, the spirit of being an open book is giving people access to vital information about how the business is performing. It’s important to do this for a variety of reason: employees want it, it provides context as to how the company is doing, and with that context people can begin to make independent and well-informed decisions about how to help us grow. If more people are making better decisions, then leaders get to make less of them (especially the smaller ones). Hence, I can continue being lazy.

The value manifests in a variety of ways. We would share company financials during Town Halls (our monthly company All Hands). We would circulate sanitized board presentations after every board meeting (sanitized because there are some discretional and personal things that not everyone needs to know). We’d discuss our unit economics in depth. Sharing details was embedded in the culture. Everyone inside the company had access to the nitty gritty as to how the company was doing. And if for some reason they didn’t have it at their fingertips, they could always ask.

I have found that people who join early stage ventures oftentimes do so to learn as much as possible. A great way to accelerate learning is to share information on what’s important to the company so people can track it and see how inputs effect outputs. They also want to have some sense of autonomy and feel like they can contribute beyond being told what to do or the confines of a specific role. Being an open book helps steepen the learning curve while improving the way people can contribute.

Being an open book also helps people make critical career decisions. They know when things are good and can get excited about growth trajectory. They also know when things are bad and they can either buckle down and dig through the muck (this is why it’s important to hire people who believe in your mission) or they can jump ship and find a more stable environment. Shitty surprises suck for employees. It’s a huge disappointment to wake up one morning and be told your company burned through all its cash and now has to shut down. It’s an even bigger disappointment to be caught totally off guard by this, or to learn about it from the press. Don’t create environments where this can happen to the people that bet a chunk of their career on you.

I will never understand early to mid-stage companies that don’t share pertinent financial information with their employees. Pending certain situations where it’s legally impossible or inadvisable, leaders shoot themselves in the foot by hiding this information. It’s not good for the company, it inhibits people from making great decisions because they don’t have appropriate context, and it’s not fair to employees.

Make life easy, treat people like adults, be an open book.

The Code Breaker

One of the most exciting things I read recently was Walter Isaacson’s The Code Breaker. I knew very little about the life sciences and gene editing and I thought the book was an excellent primer on the topic. As the S-curve of the proliferation of the Information Age begins to flatten we will enter a new era driven by innovation in the life sciences. This is because we now have the ability to eradicate genetic diseases from the human race. Permanently. The implications are vast, but the biggest takeaway is that life as we know it is about to change forever. We can now determine what genes we have. It’s the stuff of science fiction. A generational breakthrough in human ingenuity with the potential to be both liberating and cataclysmic.

One of the things I loved about the book was the prevailing sentiment amongst scientists, especially Jennifer Doudna, that curiosity is a good in and of itself: “When you do curiosity-driven research, you never know what it may someday lead to…something that’s basic can later have wide consequences.” It’s remarkably similar to software in the sense that some of the most important innovations came to fruition simply because somebody was curious about something. And those inventions become accidental building blocks for some new previously unfathomable innovation. The scientists in the book are not motivated by money, or even glory (although they are fiercely competitive when it comes to acknowledgement for their contributions), but “the chance to unlock the mysteries of nature and use those discoveries to make the world a better place.”

Another element that stood out is that the life sciences, particularly gene editing, is becoming increasingly similar to software development. Molecules are becoming the new microchips. We now have tools that scientists say operate just like word processors because of how easy they are to use. The implications of having word processor-like interfaces to edit DNA are mind boggling. The technologies have progressed so much in the past two decades that biohackers can now conduct experiments from the comfort of their own homes.

It’s not a question of if we will use gene editing in the future. It’s already happening. Isaacson goes through all of the moral and philosophical implications of being able to edit DNA. It’s incredible that we can eradicate diseases that cause millions of people to suffer terribly. It’s also terrifying that people can self-select superficial physical attributes. It doesn’t take much stretch of the imagination to understand the inherent dangers here. That said, I believe that if we have the ability to eliminate genetic disorders that cause nothing but pain and death then we should. We should help people because we can. And as Isaacson’s subjects so deftly illustrate, we absolutely can do this.

Optimizing for Luck

In January I gave a talk at DeFi Alliance about how to optimize for luck as an entrepreneur. I believe that luck determines anywhere between 25-90% of your success, depending on the industry (e.g. in consumer it’s definitely on the higher end of the spectrum).

I think of luck as seemingly arbitrary things that happen to you along the course of your life. In my experience, there’s definitely a way to increase the likelihood that these arbitrary things occur more frequently in your favor. The primary way to do this is to increase your surface area. As an entrepreneur just starting out, think of yourself and your life as a two-dimensional shape. There’s a lot you don’t know: people, information, how to do things, etc. You don’t have a ton of surface area. By increasing your surface area and transforming into a three-dimensional object, you exponentially increase the chances of becoming lucky.

These are some of the things I’ve found helpful to increase your surface area:

Share your work. I was lucky to break into tech. I graduated in 2009 in one of the worst job markets in recent history, right during the Great Recession. As an undergrad, I was the Publisher of a student-run guidebook to NYC that was distributed to incoming students across most NYC colleges. I carried copies of the book with me wherever I went. I gave one copy to one of my best friends from high school, who happened to share it with his uncle at a family reunion who happened to be John Maloney, the President of tumblr. John reached out and offered me a job doing the stuff he didn’t want or have the time to do. My other alternative was doing Teach for America in middle-of-nowhere Louisiana. While it would have been a noble endeavor indeed, my life would have likely looked a lot different. I got lucky because I relentlessly shared my work.

Partner with good humans. A good way to increase surface area is to partner with people that are great humans. What’s more than one three-dimensional object? Two of them! Solo founders live a tough life. By having more people deeply invested in your success with aligned incentives, your surface area grows. Partnering with Steve over the years has massively increased my luck.

Share your ideas. Ideas are the things that happen before you do the work. Sharing them is a great way to know where to invest your time and energy. When I was at tumblr I was going to leave to pursue an idea called It was a recommendation engine to “find and share recs with people you know and trust.” It’s a shitty idea. Tons of people have tried it, and I got enough feedback on it to dissuade me from pursuing it. I was lucky because I would have wasted my most valuable asset had I not shared it – time. was what we called GroupMe before it was GroupMe. Steve and I shared that idea before going all in. We got tons of positive feedback, quickly built a prototype in a night, and it took off immediately.

Network shamelessly. The bigger your network the more people you can share your ideas and your work with, the broader your surface area grows. We built GroupMe at a hackathon at TechCrunch Disrupt. We ran around the conference demoing the app to anyone who had ears and wasn’t totally freaked out by us. Two of those people, Charlie O’Donnell at First Round and Ron Conway at SV Angel, became our first investors and helped put together a syndicate for us.

Find your advocates. Having strong relationships with your mentors and previous bosses can go a long way. John Maloney, my boss from tumblr, told me to pursue GroupMe and that he would write a check for it. He also made the introduction to Andy Weissman who gave us our first term sheet. Kevin Ryan was the CEO of Gilt Groupe (where Steve worked) and pushed us to pursue GroupMe and take an investment from Gilt. Both of our mentors supported us and created a safety net for us to take a risk. We were lucky we had people who cared about our success and were there to help.

Pay it forward. I’ve invested in five different companies founded by previous employees of Fundera and GroupMe. I’ve helped them raise capital, hire people, and acted as a sounding board as they navigated their way from zero to one. One of them recently sold his company for more than what both my companies were acquired for combined! Doing good things for people always comes around. Help your peers and help your employees. If you pay it forward your surface area will grow: people will naturally tell their friends about you and then they will also want to work with you.

Get Alpha. One of the ways we survived at Fundera was by making sure the best brains in the industry were focused on helping us and on our board. One of our board members, David Weiden, was on the board of GroupMe. Two others, Frank Rotman and Scott Feldman, were on the board of Credit Karma. They were able to help me understand how to be successful by sharing intel on market comps, potential partners, other investors who were active in our space, etc. The knowledge and help of the best people in your industry is another vector to expand your surface area.

Always be recruiting. The same way you want to recruit great investors, advisors, and mentors, it’s even more important to recruit great colleagues. Recruiting never stops. You always need to be doing it. The only way you will be successful is if you have terrific people working on a focused problem together. Many of the best people I’ve worked with over my career I’ve spent anywhere between 6 to 48 months recruiting. Surrounding yourself with exceptional people massively expands your surface area. Their luck is your luck when you’re on the same team.

Know your exits. It’s critical to know who may buy you one day. Things don’t always go as planned. Actually, things normally don’t go as planned. No matter how many things you do to expand your surface area, you can and will still get unlucky. Forming relationships with execs at the companies that could be strategic acquirers can give you optionality when the time comes to sell. More importantly, it also increases the likelihood that someone will come and knock on your door and try to acquire you (which is usually always better than deciding to hire a banker and sell your company). Both GroupMe and Fundera were acquired by companies where I had direct relationships with the execs that had been nurtured for a long time.

Don’t be an asshole. This is the one “don’t” in the group. It’s self-explanatory. Assholes expand the surface area for bad things to happen to them. The climate for entrepreneurs has been incredible for the past 5-10 years. It has been remarkably founder-friendly. Unfortunately, that’s produced a lot of people that are super cocky and have nothing to back it up: there’s little traction, utility, value, or previous experience. Do not confuse being good with being in the hottest market at the frothiest time in tech history. Be humble. Karma is real.

Be a good person. When you care about other people, help other people, act with integrity, humility, and pay it forward, you increase the likelihood you win. Being a good person can actually be a selfish endeavor and that’s okay. In my experience, I’ve continuously seen wonderful things happen to great people. Life is not a zero-sum game, nor is success. The more people in your orbit that win, the more likely it is that you will, too. A rising tide lifts all ships so be a force for that tide to rise and you will, too.

There are plenty more things people can do to expand surface area, but this is a good start and the things I know from my own limited set of experiences. I hope you can put it to good use!

Annoying Kids

The other day one of my kids was doing something annoying. This happens. Sometimes a lot. Kids can be annoying.

I recognized that I felt annoyed, took a deep breath, and reminded myself that I am so darn lucky to have two awesome children. And that while sometimes it feels like time moves excruciatingly slowly when you’re stuck at home with a 5 and 3 year old because everyone has covid, it actually goes by so quickly in the grand scheme of things. And that in a short period of time I’ll be asking myself where the time went, wishing I could do it all over again.

So now when I find myself annoyed, I give my kids a kiss and hug and cherish the moment, try to be present, and recognize just how special this time is. There are moments with them when I consciously tell myself to save this one to the memory bank. Those have become the joy of my life.

DeFi: Fuel for the Analog World

Our current financial system is an absolute miracle. We often take it for granted, but it’s a modern marvel that hasn’t existed for all too long. It does incredible things and creates opportunities for people across the globe. But it’s also a big fucking mess. There are so many things wrong with it, and so much opportunity for improvement. Too many people are left out, it’s controlled by slow institutions, there’s little innovation (outside of fintech), and the banking system isn’t even open 24/7. Money never sleeps. How is this excusable?

So I’m long DeFi. It’s a system that’s accessible by everyone, everywhere, all the time. That in and of itself is enormously powerful. However, in its current state the primary utility of DeFi is speculation. There’s a preposterously large amount of money sloshing around the system speculating, searching for yield. But that’s about it. I haven’t seen a lot of utility beyond that. As Matt Levine said, “The crypto boom is a wild gold rush for money,” and no place exemplifies that more than DeFi. But this will change over time.

Lending is one of the most obvious places for DeFi to move beyond speculation and to other utility. Right now, almost all lending that takes place is over-collateralized, which enables people to borrow primarily for the purposes of…further speculation. If you want to know more about OCL, Frank Rotman has a great thread about it. I’m really excited about DeFi lending moving from OCL to under-collateralized lending and had some ideas as to how this could work.

One company tackling this is Goldfinch. They are essentially a fund of funds, aggregating assets in DeFi from people searching for yield and deploying it into a series of offline/off-chain lenders like PayJoy. For digital asset holders they provide an avenue to get yield outside of being a degen and for analog world lenders they are a capital source. They are effectively acting as a bridge between the DeFi crypto wealth that has accumulated as of late and off-chain lenders.

This is a neat concept because more and more assets will be held in crypto over time, and if those assets can be deployed off-chain, they can achieve yield that’s more consistent than speculating on token appreciation or investing in the next DeFi X.0 scheme. Imagine a fintech lender being able to tap into crypto wealth, or a DeFi participant being able to lend their crypto to Stripe, Shopify, Affirm or GS. Lenders sell capital, and there’s no reason the capital they sell can’t be the assets held in DeFi. It could, in theory, provide everyone across the globe access to every single asset class, and that changes the game.