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Entrepreneurship

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Your Loved Ones Might Not Like Your Becoming a Founder

I recently listened to a founder’s wife share her reaction to learning that her husband wanted to quit his lucrative job and start a company. She was angry, and understandably so. Life had recently dealt them a series of positive and negative jolts, and this would be another jolt, albeit self-inflicted. They discussed the decision ad nauseam. Ultimately, she decided to have faith and support her husband in pursuing his dream. It’s early in the company’s journey, but things have gone well so far, and she’s happy that she supported him.

Becoming a founder isn’t a decision to take lightly. People don’t discuss this as much as they should: starting a company probably will greatly affect the founder’s loved ones. Start-ups don’t have many resources, so the financial impact can be hard for a family to adjust to. Especially if the financial load is now on one person. Just as important is time. Early-stage founders put tons of time into their start-ups, which leaves less time for loved ones.

If you’re thinking about starting a company, be sure to consider and consult your close loved ones as you’re evaluating entrepreneurship. You and your team will be under an inordinate amount of stress to make the company succeed. It will be much harder if you’re under similar stress at home. In a perfect world, you want your loved ones to be your main cheerleaders and supports. They’ll find it hard to live up to that if they haven’t been included in the decision-making process.

New Networks = New Ideas

I shared some views on the importance of networks with someone recently, including how being part of different networks helped me navigate my early founder journey.

One thing I didn’t realize back then was that being part of diverse networks was valuable because it exposed me to new ideas. I learned about all sorts of things I would have never known about. Some of those ideas became transformational for me, altering my trajectory. Exposure to new ideas is something I now seek out, because it helps elevate my awareness about the world and my thinking in general.

If you want exposure to new ideas, consider joining different networks.  

A Burn-the-Ships Mentality

I listened to an investor and founder give his thoughts on what it takes to win and how he identifies winners. He described how he evaluated one of his most profitable investments: Uber. When he invested in the company early, he was betting on the founder, Travis Kalanick. Travis was intense and had what this investor calls a “burn-the-ships” mentality.

During wartime, when ships arrived at an enemy’s shore, the generals instructed the troops to burn their own ships once everyone had disembarked. The only way the troops would go home, they were told, was by taking the enemy’s ships. There was no turning back—winning was the only option.

I’d never heard an investor describe a founder in this way before, so it stuck with me. I’m all about backing founders who have a drive to win, but I’m not sure that a “burn-the-ships” mentality is a necessary or even good thing. I don’t know enough about Travis or the early Uber story to talk about them. I do believe, though, that there are ways to motivate your team to win without burning the ships.

Inbound As a Way to Find Great Companies

Last week I chatted with a few investors at Venture Atlanta. With one group, the topic of sourcing came up. I’m always curious to hear how others think about identifying the companies they’ll invest in. I noticed that most of these people had a strategy that focused on driving inbound activity. They had different approaches to accomplishing this, but bottom line, they all involved founders reaching out to investors.

Inbound activity is great for investors, but I think it can also be a double-edged sword for early-stage investors. It’s reactive. Because investors are reacting to founders, the markets they end up investing in are limited by the communications from founders they happened to receive.

Markets matter a lot in venture capital investing. It’s hard to make a big impact on the world or realize outsize returns if you’re in the wrong market (one that’s small or hypercompetitive, for example).

Inbound activity is an important part of an investor’s strategy for finding companies, but it can’t be the strategy if you want to invest in the best founders building in the best markets. You’ll likely have to spend time thinking about what markets you want to be in and then go pursue the founders in those markets.

Disconnected Networks

Last week I attended Venture Atlanta and a variety of other events throughout the week. I hadn’t been to Venture Atlanta in person in over two years, so I wasn’t sure what to expect. The events were all great, and I met some amazing people. One of the things that jumped out at me was the number of people who didn’t know each other. Said differently, last week’s events highlighted how little certain networks interact with each other.

Once I realized how many people didn’t know each other, I made a point of trying to connect people who should know each other or could help each other. Hopefully, those connections will be helpful and allow those folks to expand their networks.

I think there’s a big opportunity in early-stage entrepreneurship to connect more networks that don’t interact—locally and nationally. I’m going to spend more time thinking about how to do it.

Probability of Raising a Series A?

I listened to someone share an interesting way to think about start-up investments. This person is helping a seed-stage investor rethink their evaluation process, which included considering how big the company could be if things went well. Could this be a billion-dollar company that returns the fund, or would it max out at something smaller? They modified their approach to think about near-term probabilities. Specifically, what’s the probability that the company will raise a Series A? The logic behind this change was that most companies wouldn’t exit for more than $1 billion without raising a Series A, so why not focus on evaluating this?

It’s an interesting approach that got me thinking. The likelihood of a company raising capital from a later-stage investor is something that it’s good to be mindful of. Thinking about the probability of this happening could produce useful insights.

In the last two years, many early-stage companies raised at high valuations by historical standards. I remember seeing a seed-stage company raising at a $100-million-dollar valuation. Given these high valuations early in their life cycle, I’m wondering, what are the probabilities of these companies raising clean Series A rounds?

Will Outsiders Shake Up VC?

I had a chat with two friends yesterday about the venture capital (VC) industry. One works in the industry and the other is entering it. We debated the difficulty of breaking in to the industry, the challenge of getting capital if you’re a founder outside the VC network, gender issues, and a few other things.

One of my friends pointed out something that stuck with me. He said VCs that have been successful have accumulated unheard-of amounts of wealth at young ages (relative to historical norms). They’ve achieved this success using a particular playbook. There are certain parts of that playbook that people might not like and that are under fire now. But why change what you’re doing if it’s working so well?

If you look at the history of venture capital, you see that the industry changes when it’s forced to. Said differently, when its economics are threatened, the industry reacts. Masayoshi Son and Chase Coleman are examples of outsiders whose unusual approaches affected industry returns and caused the industry to adapt.

It’s interesting that for all the disruption and innovation VC brings about in other industries, VC itself doesn’t evolve and innovate at a faster pace. The world has changed a lot since March 2020, and I think the VC industry hasn’t innovated enough to keep up with all the changes. I think we’re due to see another wave of changes to the industry caused by outsiders.

Institutional LPs and the Early Stage

When early-stage founders building high-growth companies think of raising their first bit of capital, they think find a venture capitalist. What they don’t think about is where the venture capitalist gets the money. The people who invest in a venture capital fund are limited partners (LPs). VCs have a responsibility to be good stewards of LPs’ capital—and if they aren’t, they won’t get any more of that capital.

I had breakfast with an out-of-town venture capitalist raising a $100+ million fund that invests in seed-stage (product built, but no product–market fit) companies. They’re not investing at the idea stage, but still early. He worked at a notable fund for years, but this is the first time he’s raised his own fund. We discussed his fundraise and the LP environment. He’s been focused on institutional investors (endowments, pensions, foundations, etc.), given his relationships and experience. He’s gotten good traction with his fundraise, but he’s hearing that many institutions prefer to back a manager at fund three and beyond. They want to get to know you during fund one and two. They want to see the company’s track record and performance and build a relationship with the manager over the first two funds. Once they get comfortable with a manager, they’ll back them over a few funds.

My conversation with this manager reinforced my view that early-stage investing can present a dilemma for LPs because what they’re comfortable with doesn’t align with the flux and transient nature of the early stage.

I walked away from this conversation, and others, feeling like there’s ample capital available from folks who want to invest in early-stage companies. But the current venture capital construct isn’t ideal when it comes to matching capital to founders. I’m wondering, is this an opportunity for an alternative that institutional LPs would like, or will LPs backing early-stage companies forever not be institutions (individuals, family offices, etc.)?

How Can We Connect Atlanta’s Mini Communities?

Over the past few years, I’ve connected with lots of investors outside Atlanta interested in learning more about the city’s start-up ecosystem. It isn’t easy to understand, I’ve often heard, and they want to know why. I explain that Atlanta’s ecosystem is composed of mini communities built around similarities. Universities (Georgia Tech, Atlanta University Center, and others), neighborhoods, and coworking spaces all have their own communities. These types of mini communities are a normal part of a healthy start-up ecosystem. The challenge in Atlanta is that they don’t overlap enough. In my explanations, I say that people don’t like to leave their neighborhoods. That’s half joke, half truth. More accurately, people are less inclined to leave their preferred mini community.

Venture Atlanta is this week, and many events are taking place. Yesterday I attended two evening events given by different mini communities. An investor and a founder were tagging along with me. Both were from out of town and interested in learning about the Atlanta start-up ecosystem. As we left the first event and entered the second, one of them commented that the events felt like two different worlds. Both were attending by amazing people from mini communities who want Atlanta to win—people who were noticeably different and only minimally overlapping. As we left the last event, my two guests shared that attending the two events (which were two miles apart) and seeing the mini communities helped them understand the Atlanta ecosystem.

Legendary companies are built when high-potential entrepreneurs are matched with capital, scaling knowledge, and relationships. Atlanta’s mini-community dynamic creates network distance, which fosters inefficient matching.

I see an opportunity to supercharge early-stage entrepreneurship in Atlanta. If the number of conduits between these mini communities were to grow, the free flow of information and relationships in the city would do likewise, thus reducing network distance and increasing matching efficiency.

Liquid Investments Can Work Against You

I’ve shared my views on how short-term valuation changes affect psychology. I was reminded of them recently when I had a great dinner with two established, successful founders, one of whom recently sold his company. The topic of public markets came up, and both shared that their portfolios have lost material amounts of money. The most interesting thing they said was that looking at their portfolios regularly is frustrating. One of them even mentioned that he was nervous about checking it given the recent market trajectory. They’re both considering selling losing positions to stop the bleeding.

Liquidity is a big difference between the public and private markets (i.e., venture capital). Some view the liquid nature of public markets as a benefit. There are benefits to it, but I also see a downside. Because of the liquidity of public markets, investors can constantly check the value of their investments. When valuations fall for macro reasons (i.e., the company is doing fine), some investors may sell their investments with the click of a button. Even though the company is doing fine and could appreciate significantly in value in the future, today’s pain is too much to bear, and people sell prematurely.

Private markets are different. Investors can’t check the current value of an investment. Companies are usually valued at the last round of capital raised. As companies face hurdles or the macro market changes, the valuation is still at the latest round. Resetting the valuation usually means raising a new round or a private party transition between two parties. Neither of these options is easy. If a seller is able to coordinate a transaction with a willing buyer, some companies can have the right to block the transaction. All of this means that investors in private companies are more likely to stick it out with private investments when times get tough.

The illiquid nature of private investments makes it hard for some people to embrace them. I think this illiquidity isn’t necessarily a bad thing. For winners, it forces investors to stick with investments during hard times. As companies get past the hard times, these investors reap returns they likely would have missed out on if they’d been able to sell their investment early.