Remote Work

I had independent chats with two people who work remotely full-time, one for a tech company, the other for a non-tech company. Headquarters is thousands of miles away for both people, and they work mostly from home. The tech employee is part of a team working to complete projects but is the only person in his city working for this company. The non-tech worker is an individual contributor (he doesn’t need others to complete his work), but he has coworkers in his city (though he rarely sees them). These conversations were enlightening. The tech person loves his work, but there’s a bit of feeling like he’s on an island (my words, not his). The non-tech worker loves his work setup and wouldn’t change a thing.

I’ve been a proponent of remote work for over a decade. My first full-time hire at my start-up was someone in Europe. She was an A player with my company for seven or eight years and opened my eyes to the quality of talent available remotely. We hired more people over the years in a hybrid model. Some were in-office in Atlanta and others were remote working in various cities worldwide (including Atlanta). I made mistakes managing this hybrid team but learned a lot. The biggest learning was that some roles (and personalities) are better suited to remote work than others. Individual contributors and those who like working alone tend to thrive in this environment.

Remote work is here to stay (in some form or fashion). I think every company must figure out what that means for them and their culture.


YC = Accelerated Learning Loop

Harj Taggar discussed why being a partner at Y Combinator (YC) is so powerful for an investor. He’s done two stints as a partner at YC, so I was curious to hear his thoughts. During his interview, he shared that working with hundreds of companies a year allows a YC partner to learn more, faster, than a traditional venture capitalist can. Learning what works and doesn’t work is accelerated, and YC partners feed those learnings back into the companies—all with a goal of reducing the overall failure rate over time.

Harj’s interview made me think of what a good friend said: the faster you learn, the more successful you become. Harj’s thoughts on YC being a place of accelerated learning, which leads to more success, make a lot of sense. It’s a feedback loop of sorts. The learning is compounding with each YC cohort of founders.

This has me thinking . . . what are other ways are there to create feedback loops for outlier entrepreneurs—those outside the purview of venture capital networks and start-up ecosystems?


The Cheetah Strategy

The path to success at my start-up was product. We sold automotive products to consumers but didn’t want to buy lots of inventory. (In fact, we couldn’t.) We needed to work with manufacturers and distributors to sell their inventory in their warehouse infrastructure. We knew who the big, established players were—the ones who had the best inventory—but they wouldn’t work with us. No return phone calls, no responses to emails. They had enough business to keep them busy and didn’t want to bother with some pesky start-up.

Realizing we needed to work with partners who needed us, I went to the other end of the spectrum. I found the suppliers who didn’t have as much business and hadn’t adapted to the changing times. Those players embraced us with open arms. We learned from them, and they learned from us. Testing until we identified the optimal way to work with them, we built software to systematize and add scalability. And we provided them with reports detailing where their operations fell short of our expectations so they could improve.

We gained a solid reputation with customers and early suppliers. When we again approached the established players, they were eager to work with us. What had changed? We were no longer an unknown entity doing things differently. We had some street cred. They’d consistently heard great things about us and knew we were growing quickly. By the time our paths crossed again, they knew they needed to work with us because of the weight of the momentum we’d built in the industry. Negotiations with them were easier, too, because other suppliers had told them what they’d negotiated with us.

We ended up winning by thinking like a cheetah: we went after the slower, weaker players in our space first.

If you’re a founder trying to get something off the ground and need others to play ball, consider thinking like a cheetah. (But remember that your objective is different—your goal will be to find someone willing to work cooperatively with you, not someone to eat for lunch!)


Weekly Reflection: Week One Hundred Twenty-Four

Today marks the end of my one-hundred-twenty-fourth week of working from home (mostly). Here are my takeaways from week one hundred twenty-four:

  • VC research – I’ve been researching the origins and history of the venture capital industry. Success in venture capital can be random, but sustaining it for a long time requires intentionality.
  • Frustration – I ran up against some hurdles that set me back this week. I was reminded to push through the frustration and not dwell on the situation.
  • Good people – I spent more time this week with good people I’ve known for a long time. It was energizing and refreshing.

Week one hundred twenty-four was trying. Looking forward to next week.


The Incremental Margin

As an early founder, I’d built a manual operation and was having a hard time growing it while maintaining operational consistency. Our workflow was complex, with many potential points of failure. It was expensive, and it couldn’t scale. I figured technology could help make our processes consistent so we could grow. There were other benefits I didn’t realize.

After we built technology, things got predictable. I began to model growth scenarios, and something jumped out at me: the incremental margin. As revenue increased, our costs went up, but not nearly as quickly as revenue did. With every additional dollar of revenue we earned, a bigger fraction fell to the bottom line. Said differently, the more we grew, the more profitable we became —mainly because of the efficiency gains from the software we’d built. For the first time, I could clearly see the profit potential of the business.

Seeing the impact that the incremental margin could have on the business was a big aha moment. It was as if I could see into the financial future of the company and I just needed to figure out how to grow to get there.  

Side note: I had assumed that customer acquisition costs would stay flat, and that assumption proved incorrect years later because our market wasn’t growing. Nevertheless, thinking in incremental margins is something I do to this day.


Pick the Right Market If You Want to Scale Your Start-up

I talked with a founder/investor and another investor today, independently, about scaling start-ups. Finding product–market fit is the first hurdle. After that, scaling your solution can be difficult. We discussed various ways to go about it, with markets dominating both conversations.

Markets play an outsize role in a start-up’s ability to scale. I should know. When I was a founder, my team and I realized we were in a big market. At the time, it was $30+ billion. We figured that was more than big enough for us to build a huge company. One percent of $30+ billion would be $300+ million in revenue. We figured that getting 1% market share was more than reasonable. What we didn’t spend enough time on was understanding the trajectory of the market. It was a decades-old market that was flat, meaning it wasn’t growing. We eventually realized we had to steal customers from established competitors. (That didn’t go over well. We upset many people.) We scaled the company to $10+ million. (So much for $300+ million.) There were several reasons for that, and market was a big one. Stealing customers is difficult if your solution isn’t 10X better than the competition (ours wasn’t).

My big takeaway from that experience was that market size matters, but the trajectory of the market matters too. A fast-growing market can be a great opportunity for founders, even if it’s small now. If you find product–market fit, the market’s growth can pull the start-up along, making it easier to find customers and scale the company.


Self-aware Idea Guy

I caught up with a founder friend today. He shared his vision for his next thing. It’s big! It could have a huge impact if he’s successful. I asked him some questions about execution. Without hesitation, he told me they’re important questions and they’ll get answered, but that’s not his strength. He’ll bring on another leader strong in execution and details. He didn’t sugarcoat anything. He owned his weakness and has a plan to address it.

I love how my friend is self-aware. He’s an idea guy, a big-picture thinker who enjoys thinking about the future and what’s possible. He knows this and stays in his lane. He recognizes that a team is required to turn his vision into reality and is eager to partner with someone strong in the areas where he’s weak.

I’m excited to see him start working on this new thing and can’t wait to see the team he assembles. I suspect it will comprise people who complement each other and who will help him do amazing things.


Strategy Session

For several months, I’ve been gathering information for a personal project. I wanted help digesting all the information, and I wanted holes poked in what I’ve done so far. So, I spent today in a multi-hour whiteboard session with others. I wasn’t sure what to expect, but I was excited heading into this meeting.

As it turned out, it was very helpful. It was great to get the perspectives of credible outsiders who could look at the problem and the information gathered with fresh eyes. We identified some great insights and are energized about the problem.

Today’s session reminded me of the strategy sessions I had as a start-up founder. There’s a problem to be solved, we believe it can be solved, but the solution isn’t obvious. After debate and a thoughtful exchange of ideas, a solution is formulated.

Today was a reminder that I need to do these sessions more often.


Larger Funds Can Complicate Life for Emerging VC Fund Managers

I want to follow up on yesterday’s post about larger VC funds creating a dilemma for established firms. I chatted with an emerging manager recently. Raising his first fund wasn’t easy. After eighteen months, he hadn’t hit his $25 million fundraising goal and stopped at $10 million. That first fund is performing well, and he went out to raise his next fund a few years later. He wanted to raise $50 million but ended up with $60 million because of outsize demand from limited partners who wanted to invest at the ground level of amazing companies.

When we spoke, he was happy the second fund is larger but, at the same time, on the horns of a dilemma: he can’t deploy fund 2 using the same strategy he did with fund 1. He gave me some simple math. (Note that he ignored reserves for follow-on investments and other variables for the sake of getting his point across.)

He wants to invest at the ground level and aims to be the first check or in the first round of capital raised by early companies. From fund 1, he could write a $500k check—5% of his $10 million fund. He could make 20 of these investments, which is achievable, and deploy the full $10 million. The valuations were reasonable, and if one investment performs well, it could return the entire $10 million fund.

With fund 2, though, to write 20 checks each representing 5% of the fund, each check must be for $3 million. But the early companies he targets don’t need $3 million! Their first rounds are usually much smaller.

He now must choose among what he views as not great options: overcapitalize 20 early founders with $3 million at inflated valuations and negatively impact fund returns, stick with $500k checks and find 120 companies, do a hybrid of the two, or invest in 20 slightly later-stage founders (i.e., not at the ground level) at reasonable valuations.

This manager has done a great job of finding, capitalizing, and supporting founders during the earliest part of their business cycle. He’s successfully investing at the ground level of some amazing outlier companies. His strategy worked well for fund 1, which led to fund 2 being larger. He now must adjust his strategy because of the larger fund size, which could hinder him from supporting founders at the ground level. The math (simplified here) demonstrates how raising a larger fund can complicate backing founders at the earliest parts of their journey.


The Dilemma of Larger Venture Capital Funds

It’s been interesting to watch the last few years of venture capital. The number of firms raising larger funds appears to be increasing. This sounds good until you consider the math of venture capital funds. Most early-stage funds consider an investment a winner if it returns the entire fund or more. If you raise a $500 million fund, you’re looking for an investment in a single company to return $500 million or more. The number of companies capable of such a return is small, so when you find one, you must capitalize on it. If you don’t, a fund is less likely to generate a meaningful return for its investors when the companies that will fail are factored in.

Instagram is a well-known acquisition. It was founded in 2010 and acquired in 2012 by Facebook (now known as Meta) for $1 billion. Andreessen Horowitz invested $250,000 in Instagram’s early seed round and realized $78 million at the time Instagram was sold. That’s a 312x return. The challenge is that Andreessen made the investment from a $1.5 billion fund. Instagram was the investment of a lifetime, but it didn’t return the fund. It returned less than 6% of the fund. That means Andreessen would need to make 19 investments like this one to return its fund. That’s not likely. Do note that Andreessen made decisions specific to this situation that reduced the firm’s return, but this nevertheless illustrates the challenge of large funds investing at the ground level of a company.

The larger the fund, the larger the check the fund needs to write (unless it increases the number of checks) for a single investment to return the fund. When VC firms raise larger funds, many choose to invest at a slightly later stage (think seed instead of pre-seed or series A instead of seed) because the larger check size makes sense given the number of checks they want to write out of that fund. I think this leaves a void to be filled. The question is, what’s the optimal way to fill that void AND still generate a meaningful return?


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