Figuring Out My Next Chapter: Venture Capital

I’m happy to announce that I’ve joined Outlander Labs as a venture partner. Outlander is a new venture capital firm in Atlanta. We’re focusing on investing in early-stage entrepreneurs in the Southeast.

So, How Did I Get Here?

Nineteen months ago I began thinking about my next chapter. I was ready for something new but unsure what it would be. I wanted to work on something significant and figured it would be worthwhile to take my time figuring it out. I had no idea what this process would look like, where it would take me, or how long it would take. It’s been full of twists, turns, frustration, and uncertainty, but overall it was a great journey. Here’s how everything transpired:

Phase One: What Am I Great at and What Problem Do I Want to Solve?

Months 1–8 (Feb. ’19–Sept. ’19)

  • Unique Ability – I read this book years ago and was intrigued. The premise is simple. Everyone is amazing at something that comes so naturally to them that they don’t realize how unusual their talent is. People close to them have to point it out. I followed the steps in the book and asked those close to me for their insights. This sparked once-in-a-lifetime conversations. So glad I did it! I heard lots of “I’ve always seen this in you, but never shared it because you never asked.” Just as the book predicted, I saw a pattern in this feedback.
  • Problem hunting – I researched problems that I noticed and talked to venture capitalists about problems they saw in real estate, business communication, e-commerce, and a variety of other areas. The conversations with venture capitalists stuck with me and I began researching more about early-stage investing in my free time.
  • Experience sharing – I reached out to entrepreneurs who had begun new chapters of their lives after building successful companies. Lots of lunch meetings and coffee chats over many months.
  • StrengthsFinder – I participated in a retreat where I was introduced to this concept. What I learned about myself and how I operate was surprising. The approach was different from the one in Unique Ability, but I saw similarities in the results. I wanted to dig deeper into this.
  • Giving back – I began connecting with rising entrepreneurs to help however I could. I usually made introductions and shared lessons I had learned over the years. Mainly this was in informal chats.

I felt scattered during this phase. I wasn’t able to clearly articulate what I wanted to do, which was frustrating. I’m sure people I spoke with thought I was all over the place, but they listened and I appreciate that. It felt like things were moving really slowly. In hindsight, I think that was just a function of the stage I was in. Things were coming together, but that was hard to recognize. My activities helped narrow my focus. I ended phase one clearly understanding what I’m great at and the problem I’m most passionate about solving (and qualified to solve).

Unique ability: Identifying and analyzing improvement opportunities so potential can become reality

Problem: Some early entrepreneurs in Atlanta fail unnecessarily. They’re capable and have good ideas. But they’re hindered by big knowledge, relationship, and capital gaps (I call them the big three). It takes them significantly longer than people with comparable skills but smaller gaps to achieve meaningful traction. They often run out of runway (money and/or time) before they find a solution customers will readily pay for (product–market fit).

Now I needed to figure out how to use my unique ability to solve this problem.

Phase Two: How Can I Solve This Problem?

Months 9–10 (Oct. ’19–Nov. ’19)

  • Coaching – Because I wanted to dive deeper into StrengthsFinder, I engaged a coach who specializes in this area. I’ve never had a coach before, and the experience far exceeded my expectations. My coach is a great sounding board and accountability partner. And she’s pointed out seemingly small things that I should dig into. I’m still working with her.
  • Giving back – After identifying the big three, I wanted to focus on helping early entrepreneurs overcome them, but I wasn’t sure how. I continued sharing my experiences and making introductions. I started working more closely with founders and I gained valuable insights into specific hurdles and how they’d tried to overcome them. This ended up being customer discovery, in a sense.
  • Capital – I looked for ways to fill this gap for early founders. I researched angel investing, venture capital, crowdfunding platforms, etc. I connected with local investors and attended investor group meetings.
  • Community – I attended community events aligned with early-stage entrepreneurship and investing. The biggest events in Atlanta happen around the same time, so this was a whirlwind. The ability to connect with many people at one large event proved clutch.
  • Relationships – I continued meeting with other entrepreneurs and began meeting with angel investors and venture capitalists as well. I shared what I was learning and the big-three problem I saw. My thoughts were still rough, so their insightful feedback gave me lots to mull over.

I ended phase two with a few key learnings. I enjoyed working with early-stage entrepreneurs and helping them think through ways to overcome roadblocks. But while I found this fulfilling, I questioned the impact I could have on my own. I wanted to help entrepreneurs in a more scalable way and recognized that I would need to include others.

Investors are uniquely positioned to help founders fill the big three. They have capital, vast networks, and knowledge amassed from evaluating and advising numerous companies every day.

Angel investing is interesting but would be difficult for me to optimize in Atlanta as an individual. I wanted to fill the capital gap through a team approach.

Helping entrepreneurs by providing capital sounds easy, but it isn’t. A lot happens between meeting a founder and writing a check. Even more happens to support the founder after the check is cut. I was able to quantify how much I didn’t know in these areas.

Working alongside investors to help entrepreneurs felt like a good fit. We could collectively solve the big-three problem and I’d get to use my unique ability. I needed to fill my investing-knowledge gap, though.

Phase Three: Learning about Investing

Months 11–13 (Dec ’19­–Feb ’20)

  • Relationships – I shared my views on the big three and asked for perspective from other entrepreneurs, investors, and anyone who would listen. Some agreed with me and some didn’t. These conversations were helpful. I learned that I needed to do a better job of communicating the big-three problem with conviction.
  • Venture capital – I needed to begin filling my knowledge gap. I reasoned that working closely with a fund or investing in a fund were the two best approaches. As I met with funds, I realized that I probably wouldn’t get the opportunity to work alongside an established fund because I lacked venture experience (my knowledge gap was too high a hurdle). I became a fund LP instead (that is, I invested in a fund).
  • Giving back – I continued to mentor and advise. At the urging of others, I decided I would begin sharing my experiences in a more structured way via daily posts.

I ended phase three with an enhanced understanding of venture capital. Venture capitalists can invest in any one of many different stages of a company’s life cycle. I concluded that venture capitalists focused on pre-seed-stage investments are best positioned to help entrepreneurs overcome the big three.

Investing in funds ended up working out well. I got an education on fund performance metrics, investment thesis, investment team experience, etc. It was eye-opening and a great relationship-building exercise. But there was still a ton I needed to learn. I also lacked wide-ranging relationships in the industry. I determined that filling both gaps would likely require a multi-year commitment.

I concluded that working alongside pre-seed venture capitals would position me well to solve big-three problems. But I first needed to fill my own gaps and learn more about investing. There were more funds active at the pre-seed stage outside Atlanta, specifically in Silicon Valley, L.A., New York, and Boston. I set out building relationships with individual venture capitalists in those areas. I wanted to learn from them and also make them aware of investment opportunities in Atlanta.

I knew I wanted to work closely with pre-seed venture capitalists from the coasts and needed to build those relationships. I didn’t want to leave Atlanta, though, so it would be an uphill battle.

Phase 4: Finding the Right Partnership

Months 14–19 (March ’20–August ’20)

  • Venture networking – I began sharing my views on Atlanta investment opportunities and how addressing the big three could accelerate success in Atlanta. I was surprised to learn that there’s a strong desire by venture capitalists on the coasts to invest in Atlanta.
  • Giving back – I continued to work with founders and became an official advisor (unpaid) to a few founders. I made good on my promise and began sharing my experiences via daily posts.
  • Founder networking – I shared my desire to help early founders by transitioning to venture capital. Some founders were supportive; others were skeptical. As builders, most of them wondered why I don’t just build another company. I enjoyed having these conversations with my peers at this stage of my exploration. Debating the merits of building versus investing in a company was enjoyable.

The first week of March, I shared the big-three problem and my desire to connect with experienced West Coast investors with a founder friend. He suggested that I meet with the Craigs. Leura and Paige Craig had recently moved to Atlanta from L.A. They’ve jointly made over a hundred early-stage investments in startups, most at the pre-seed level. A few of their early investments (Twitter, SpaceX, Lyft, Postmates, Bird, and Wish, among others) reached unicorn status (a value over $1 billion).

Over many conversations, we shared our views on Atlanta’s potential. It turned out that they overlap in many areas. There are many founders capable of building amazing companies in not just Atlanta but the entire Southeast. With the right support, the sky’s the limit for them. The right support at the pre-seed stage is the missing piece. We talked a lot about solving for that missing piece.

I enjoyed hearing their perspective because they’ve helped founders overcome the big three and go on to achieve large-scale success. During these conversations, I again realized how wide my gaps were.

Paige founded an L.A. venture capital firm and has intimate knowledge of launching L.A.-based accelerators as well. Leura and Paige see a venture capital fund with enhanced accelerator-like support as the missing piece in the Southeast. I liked their idea.

Over many months they executed on their vision to form Outlander and invited me to join their team.

And here we are today.

I’m excited to be part of a team focused on accelerating founders’ success. I’m hopeful that we will help usher in a new wave of successful entrepreneurs in the Southeast!

Disclaimer: This may look like a well-thought-out process, but it wasn’t. To write this, I reflected on the journey and broke it into phases to make it clearer. I wasn’t conscious of phases while I was living it; rather, I was figuring it out as I went along and adjusting as I learned. It was an extremely iterative (and sometimes disorganized) process until the very end. Continually speaking with others was critical to making the right adjustments, and it led to unexpected events (like meeting Leura and Paige).