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).

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As an early-stage entrepreneur, I didn’t fully appreciate the value of nurturing relationships. I thought that if I worked hard and presented a logical case, others would want to work with me. Eventually I realized that I was missing an important part of the equation.  

I wanted CCAW to enter a new segment of the automotive parts industry. It was a massive market and where I saw our growth occurring. We invested in creating a better technological approach to selling these products, but I couldn’t get any vendors to listen. None of them wanted to give us a shot. The conversation would go something like this: “This is great, but we don’t know you” or “How do I know you can do what you say you can do?” I tried for months to get someone to give us a shot. No dice. Then I finally got a lucky break. Someone I had worked with moved to a new company that we’d been eyeing as one we’d like to work with. He vouched for us and described the fruitful relationship we had with his previous employer. An established relationship opened a door that had been closed for months. All of a sudden we got the green light to start doing business with them. We quickly grew the business to hundreds of thousands of dollars a month. The vendor was blown away.

There were tons of things I did wrong in this situation, and the biggest was not establishing relationships with these vendors ahead of time. I should have been telling them about my vision and how we were going to make it a reality through innovative technology. I should have been sharing the success we’d had in other product categories. As we built the technology, I should have been updating them. If I had done these things, I’ll bet the conversations would have been much smoother when we were ready to go live with the new category.

I learned that a great idea can be dismissed if it comes from a stranger. And that the same idea (or a worse one) from someone known and trusted can be welcomed on the basis of the strength of the relationship.

If you’re trying to do something that can’t be done without someone else’s buy-in, make a point of cultivating a relationship with them before you need them. They’ll be more likely to want to work with you.

One thing I’ve noticed about my entrepreneurial journey is the role that serendipity has played. I’m a planner by nature and that’s helped me a ton, but I’ve also benefited from more than my fair share of unexpected positive events. For example, I was once in the kitchen of our coworking space casually chatting about what I was working on and a role I was looking to fill. The person I was talking with—whom I didn’t know well—knew someone he thought could be a good fit. He introduced us, we agreed, and that key hire accelerated our strategic progress over the next year.

I have many more stories like this. And I’ve realized they have something in common: being open with someone preceded, perhaps triggered, serendipitous events. Talking about my successes and failures and what I was thinking has often been followed by positive, seemingly random events.

I’m an extremely private person, so telling other people my business doesn’t come naturally. Over the years, though, I’ve learned that the pros of sharing far outweigh the cons. Serendipity is one reason for that.

Wherever you are in your journey and whatever you’re working on, consider sharing it with others. You never know where those conversations could lead!

Happy Labor Day!

I hope everyone had a safe and healthy holiday!

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Many years ago I sat with a successful entrepreneur in Atlanta. I laid out CCAW’s business model and where I thought the company was headed. The entrepreneur told me that our customer acquisition strategy was flawed. I disagreed and listed all the reasons it worked.

Years later I realized that how we acquired customers wouldn’t get us to our next revenue milestone. I had missed the value in that conversation. I was thinking about my company’s current state. The entrepreneur was thinking years ahead. He’d lived what I would soon face and was trying to warn me. I didn’t understand that because I had tunnel vision. I heard what he was saying but didn’t wonder why he was saying it.

I wasn’t looking for feedback (even though I said I was). I was looking for confirmation. I wanted to hear that what I was doing was right. Looking back, I realize the error in my thinking. I should have been searching for truth and open to it coming from anyone credible. I had been working so hard for so long that it was tough to swallow when someone pointed out that the blood, sweat, and tears I’d poured into something were all for nothing. I often didn’t want to hear it. What I should have done was listen to the feedback and digest it. If it was valid, I should have figured out how to incorporate it.

Entrepreneurs can have very strong views. It’s part of what differentiates them from others. But it’s a fine line and they should be careful not to cross it. Smart entrepreneurs continue to have strong opinions, but they are open to adjusting them when presented with credible new information. To succeed in the long run, they must be flexible and adaptable.

The next time someone credible gives you feedback that you’d rather not hear, don’t reflexively dig in. Listen actively. Ask follow-up questions. Digest the feedback. You never know, they could be pointing out something that could change your trajectory!

I’ve been thinking about communication a lot over the last year. I believe that how small and medium-sized businesses communicate with customers needs to change, especially post-COVID-19. I can’t wait until a talented entrepreneur solves the B2C problem! I’ve recently spent time analyzing how I communicate. I spend tons of time in Zoom, email, Slack, texts, and a variety of other channels. Managing all of this every day consumes more of my energy than I’d like.

I started thinking about how serious this is. I’ve said numerous times publicly that a solution to a problem is more of a nice-to-have (versus a must-have) if people affected by it haven’t taken steps to solve it. Of course, that applies to me too, so I identified what I’ve done to alleviate this problem. I’ve tried a variety of hacks over the years, from implementing software tools to removing myself from some communication channels. I’ve stuck with one hack and expanded my use of it: multiple inboxes.

I get a decent amount of email, but the importance of it varies wildly. Some messages should get a response immediately, while others deserve only a glance when I have serious downtime. Sorting through all of it was a challenge. So, like many other people, I created multiple accounts for different purposes. I have a personal email address for close friends and family. I have a work email address for close professional relationships. I have an email address for newsletters and interests. I have an email address to capture inbound communication from social channels (LinkedIn and others). There are a few others, but you get the idea. Some I check every day, while others may get a glance once a month.

This method helps address (not solve) my problems. It’s very manual and far from ideal, but it’s what I’ve been doing. I know lots of other people who use a similar approach. There are features inside Gmail and other email platforms that address some of the pain points, but to me they aren’t ideal. Email clients like Mail and Outlook don’t do it for me either. Through research, I’ve found a few things that may address some of my pains. I’ll be testing them in the near future. Hopefully I’ll find a silver bullet. Ideally, I’d like something robust that addresses the following high-level issues:

• Privacy – I don’t want important email addresses on email marketing lists.
• Prioritization – I’d like communication from people who are important to me prioritized.
• Aggregation – I’d like messages from various accounts and channels in one central place (maybe even one view).
• Segregation – I’d like some sort of segregation, although I admittedly don’t know exactly what that would look like.
• Presentation – I’d like everything presented in a clean easy-to-digest manner.

There’s a list of features I’d like too. Right now, my hack puts the onus on the user—me—to manage multiple accounts, channels, etc. It’s doable but, some days, draining. My energy could be better used. It’d be nice to find a tool that does all this in a beautiful way that makes communication via a variety of channels easy and enjoyable.

If you have any suggestions for tools or hacks, please share them. I’m all ears and actively looking to solve this problem!

Today marked the end of my twenty-fifth week of working from home (mostly). Here are my takeaways from week twenty-five:

• Holiday weekend – I’m excited about having some downtime. I wish we weren’t in a pandemic so I could spend it with family and friends. Regardless, I’ll enjoy the time off.
• Time blocks – I’ve continued blocking out time on my calendar. I made progress on bigger projects. I’m improving!
• Giving back – I spent time giving back this week by talking with rising entrepreneurs, and I really enjoyed it. I’m looking forward to doing more of these talks.

Week twenty-five was a good one. It was very busy and I’m looking forward to a three-day weekend.    

I’ll continue to learn from this unique situation, adjust as necessary, and share my experience.

Today I had a good conversation with an investor. I said that I always wanted to be an entrepreneur but fell into the world of tech. She described how she ended up falling into being an investor. Our journeys were very different, but there were similarities. The most obvious one? Passion.

Both of us discovered something we were passionate about. We didn’t initially know exactly how we would act on our passion, but we knew that passion needed to be the foundation of whatever we did. I was passionate about entrepreneurship, having gotten a taste of it with side hustles in high school and college. Continuing to feel strongly about it, I decided to give it a try. When I left corporate America, I wasn’t sure where the journey would take me. But I believed that as long as it included me being in an entrepreneurial environment, I’d be fine.

Fast forward a few years. I ended up in circles that included Atlanta entrepreneurs with tech backgrounds. I developed relationships with them and learned about tech (I was the definition of an untechnical founder) through those relationships. What they exposed me to opened my eyes. I eventually realized how tech could accelerate CCAW’s growth and made it the core of the company.

I didn’t set out to be an entrepreneur in the tech world. I fell into it. And I’m glad I did. I’ve met amazing people and learned what’s possible with the help of tech.

I never would have described myself as the kind of person who falls into things. I like to think I’m more of a planner. But embracing my passion and being open to where it took me led to an amazing entrepreneurial journey. I’m excited to see where it takes me next!

Today I was the (virtual) speaker at the Founders Journey Lesson Lab for the latest cohort of It Takes A Village. The program is a pre-accelerator focused on helping female founders and founders of color be successful. The program lasts four months and culminates in a graduation/demo day event.

I chose an informal approach that allowed for a candid conversation. I shared my background, my transition from corporate America, and the highs and lows of my CCAW journey. I also learned more about each founder, the problem they’re solving, and what they’re currently struggling with. It was a good conversation. At the end, I let the founders ask me anything.

One of them asked me a pointed question.  He wanted to know why he’d never heard of me before today and how he could find more founders of color like me who have experience building sizable companies. He said that hearing from someone he could relate to who has built a big company was inspiring. He wants more inspiration and to learn from the experiences of other successful founders of color. He doesn’t know where to find us.

I absolutely loved his question because it hit on a very important area where I’ve fallen short. Here’s how I responded:

• Personality – I’m a private person by nature and don’t like the limelight. I shy away from attention because it makes me extremely uncomfortable. But, through conversations with others, I’ve realized how impactful my journey can be. This far outweighs my personal comfort. I’ve started telling my story more.
• Heads down – Founders trying to build something big don’t have a ton of free time. They’re busy building a business. In my opinion, founders who devote time to giving interviews and getting press do so at the expense of their company, which will make substantially less progress because the founder isn’t as focused. Because founders building something great aren’t out and about and you don’t read about them, you don’t know they exist.
• First gen – Tech founders of color who started a decade or so ago (I call them the “first gen”) didn’t have a blueprint. No coworking spaces (e.g. WeWork) and few accelerators were available in Atlanta. It was a different time and we figured it out as we went. We did the best we could with the information we had at that time and learned as we went along. We got some things right and some things wrong. Some (not all) tech founders of color are realizing, looking back, that we made a mistake. We were too heads-down trying to make sure we didn’t fail. We didn’t spend enough time sharing our experiences in our community.

I’m so glad that founder asked that question. He was spot-on. The question reinforced that I need to continue doing more chats like the one today. No excuses. I should have shared more over the years. I’ve pledged to do better. I’d like to inspire and motivate rising founders of color to do something great. And I hope that other founders of color do the same if they can.

From those to whom much is given, much is required!

When I talk to founders, I like to understand what they view as their core business. What’s at the heart of their business, and what parts of the business support that core? For example, Target is a retailer, but it’s built a sizable logistics operation to move products.

As a business grows, it’s likely to need the support of many non-core functions to be successful. When you’re the size of Target, this isn’t an issue—you’ve got the resources to execute in all areas in-house. In a company’s early stages, though, that may not be the case, and founders should think hard about what they should and shouldn’t do in-house.

At CCAW, I recognized early on the critical role that fulfillment warehouses played in supporting our core function of selling automotive parts to consumers. I also knew we’d need multiple warehouses in our network and that running them was a huge undertaking. I visited a few warehouses and interviewed their owners. The upshot? I decided I didn’t want CCAW in the business of operating warehouses. Instead, I decided to outsource this function. We partnered with folks who did own warehouses to leverage their infrastructure and operational know-how. Sure, we had to learn how to work with their processes and systems, but that was relatively easy. In the end it worked out and we built a network of nearly 100 warehouses.

I knew the problems people had buying auto parts and had a vision for how to solve it through processes and technology. Warehouse fulfillment wasn’t part of our secret sauce. Recognizing that it was non-core and that there were tons of companies who did it far better than we ever could (and that we didn’t have the money to do it even if I wanted to), I chose to outsource it.

Now, I’m not saying that every newish company should outsource everything that’s non-core. CCAW’s solution is just an example of one way to deal with the core-versus-non-core issue early on when resources are limited. There’s no right or wrong way—only the way that’s right for your situation.

Entrepreneurs should have a clear idea of what their core business is and make sure that other areas of the business support it.