I recently spent time chatting with an entrepreneur. I wanted to connect with him because he’s in a non-tech sector I’m interested in getting more involved in. As we chatted, I realized that he has his finger on the pulse of what’s happening in a niche corner of his sector. He understands where it’s going, too. He’s been able to spot opportunities earlier than others and create solutions based on those opportunities. The key to his success is being at the ground level of this niche in his sector, spotting an opportunity early, and executing on what he sees.

The conversation helped me realize the scale of success this entrepreneur could have in the future. I wondered if he recognizes the potential and knows what’s keeping him from getting there. As we chatted, he shared that he does recognize the potential in what he’s doing. He explained his vision of where he wants to be and quantified what success looks like for him. Then he shared what’s holding him back:

• Capital – Executing on the opportunities he identifies requires capital. He’s got some personal capital but needs more to execute on larger opportunities. He doesn’t know how to access investor capital (not venture capital).
• Structure – He knows how to execute profitably on the opportunities he finds using his own capital. He doesn’t know how to structure deals that involve outside investors. He’s not sure what waterfall (i.e., profit sharing) or other deal mechanics are available to be used or how they should be combined to attract investors.
• Presentation – He understands why something is a good opportunity because of his positioning at the ground level and is confident executing with his own capital, but he isn’t sure how to present the opportunity to investors who don’t have their boots on the ground like he does.
• Back-office admin – He hates dealing with accounting, tax filings, entity formation, and a variety of other back-office tasks. It’s a burden that takes time away from finding and executing on opportunities. He does some of this himself and outsources some of it.

He candidly said that in a perfect world, he could get these things taken care of by someone else, focus on doing what he’s great at—finding and executing on opportunities—and take his business to the next level quickly. He realizes that a perfect world isn’t likely to appear. He plans to tackle all of these but realizes it will take time.

This entrepreneur is likely on the cusp of breakout success. I wonder how many other smaller entrepreneurs with “spotter” abilities exist and what solutions are out there to serve the needs of this group.

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I chatted with a founder recently about personal growth and about great founders constantly leveling up as their company grows. He asked a good question: how do I recognize personal growth opportunities?

It’s simple for me—I’ve got one when I’m faced with an important task or challenge that I really don’t want to do. I’ve generally got a list of various things that I need to get done. The one that makes me cringe or that I dread doing is the one that’s likely to lead to personal growth. It’s not 100%, but it happens more often than not when I get that feeling.

I’ve learned to lean into the things I dread with the hope that I’ll grow from them.

It’s often seven or more years before a start-up has a material liquidity event such as an IPO or acquisition. Founders should be comfortable with a journey of that length if they want to pursue entrepreneurship.

I recently had a chat with a venture investor who considered starting his own venture capital firm. One of the main reasons he hasn’t is the realization that it will commit him long-term. It will likely take twelve to twenty-four months to raise the fund. Funds usually have a ten-year life cycle, so once he begins investing that capital into start-ups, he’s committed to managing the fund for a minimum of ten years. That’s an eleven-year-plus commitment he’s not willing to make. Instead of writing larger checks from a VC fund, he plans to write small angel checks. He’s putting more of his own capital at risk, but he wants to preserve flexibility over the next decade.

This investor has deep domain experience and a strong network in a particular sector. Any early-stage founder he works with will get a tremendous amount of help and is more likely to achieve product–market fit.

Listening to this got me thinking. I wonder how many seed-stage venture investors (current or aspiring) who could help companies find product-market fit avoid starting a venture capital fund because of the decade-long commitment.

The rise of remote work led to many people and companies leaving high-cost coastal cities. This redistribution of talent has changed how early-stage venture capital is deployed. Before, investors would invest only in entrepreneurs whom they could meet in person. Many investors preferred to not travel, so founders migrated to cities with a high concentration of venture capital investors. But the pandemic and the redistribution of talented entrepreneurs changed this. Investors now regularly invest in founders whom they’ve met only over Zoom.

I’ve been thinking about the tech layoffs by large companies like Amazon and Google and what they’ll do to the distribution of talent. I suspect that a material number of people laid off by these companies will rethink living in their high-cost cities, especially if their job was the main thing keeping them there.

I could be wrong, but if this does play out, I’m curious about how venture capital will adjust. If a lot of talented founders no longer want to reside in the Bay Area, for example, how will these firms adjust? Will they continue to stay heavily concentrated in places like the Bay Area and do even more investing over Zoom? Or will they rethink where their firms or their firms’ investors live?

Earlier this month, I shared my predictions about tech layoffs changing the risk/reward dynamic in favor of entrepreneurship. Today, Microsoft announced that it’s reducing headcount by 10,000 people through Q3 2023. This is on top of other sizeable layoffs announced in the last few months by Amazon, Salesforce, and Facebook.

As more tech workers capable of building products are laid off, the risk/reward calculation tilts more in favor of entrepreneurship for some of them. This could be the year that many of these people bet on themselves.

“Start-ups die of suicide, not murder.” It’s a common saying. It means that most start-ups fail because of self-inflicted wounds like bad decisions, not competition. This is true, but even so, it’s critical for early-stage founders to know the competition when pitching investors.

Investors backing founders at the spearhead of company formation want to back someone who understands a problem and the market for it better than anyone else. They expect the founder to have identified something others don’t see that will allow them to succeed. Part of this process should include understanding existing solutions and why they don’t adequately serve the market. That doesn’t mean you aim to mirror what your competitors have done. It does mean you know how your solution will create more value than competitors’.

If you’re an early-stage founder and you don’t know your competition or can’t speak to how your solution is superior, you’ve diminished your chances of getting capital from investors.  

A few months back, I shared Reid Hoffman’s belief in keeping his expectations of meetings low to allow for serendipity. That really stuck with me, and I’ve embraced it, which has indeed led to some serendipity. Since then, I’ve been thinking about how to lean into encouraging more serendipity.

I’ve started to think about how to make room for serendipity through my normal nonwork interactions. I’ve landed on something that’s worked. When I’m doing normal everyday things, I now try to go to new or unfamiliar places to get exposure to new establishments, neighborhoods, and people. A simple example is dinner. Most people have their go-to restaurants and neighborhoods. These places are where they’re comfortable and what they know. Instead of sticking to your favorites, find new places (preferably with good reviews) in an area you don’t frequent. While you’re there, try to understand the people and the area.

I recently had dinner in a part of town I don’t usually go to. The place has good reviews, so I was excited to try it. Instead of grabbing a table, my companion and I chose to sit at the bar. Because we did, we had amazing conversations. The bartender gave us a history of the restaurant and its ownership. And we met another couple at the bar who build custom homes. They gave us a boots-on-the-ground perspective of the Atlanta housing market and shared some information we otherwise wouldn’t be aware of. We all agreed to keep in touch.

Serendipity, by definition, happens by chance, but you can be intentional about increasing the probability of it through your decisions about everyday activities.

Someone mentioned a quote to me this week that stuck with me:

Take a simple idea and take it seriously.

I did some digging and found that the quote is attributed by many people to Charlie Munger, but I’m not sure whether it originated with him.

When I read this quote, it reminds me that focus can lead to outsize outcomes. Successful people often had a simple idea at the core of their success. The idea itself often wasn’t earth-shattering—it was how seriously they took it that made all the difference. They thought deeply about it—to the point that they became fanatically intense about it. Eventually, they shifted their intensity to executing on their idea. Execution is often the hardest part, but because they had such conviction, they pushed through challenging times that would have caused others to throw in the towel. When the dust settled and they looked back, they’d taken a simple idea that other people probably also saw to a new level because they focused intensely on it.  

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Last week, Fred Wilson shared his predictions for 2023. Fred’s a well-known VC and general partner at Union Square Ventures. His thoughts on start-ups in 2023 were of interest to me. A few points that founders should take note of:

• 2023 will be a tough year for start-ups. As money-losing companies, many avoided raising in last year’s difficult environment. They’ll be forced to raise this year as their cash dwindles.  
• VCs have ample capital to invest but will be more selective. Companies with product–market fit, strong teams, and good unit economics will be able to raise. Start-ups that don’t have these things will struggle to raise, regardless of valuation, and many will fail.
• Valuations will return to the levels of 2015 or so. Seed rounds will be around $10m, Series A rounds around $15–$25m, Series B rounds around $25–$50m, and growth rounds capped at 10x revenue.
• Lower valuations will lead to flat rounds, down rounds, inside rounds, and lots of structure in the rounds. CEOs and boards should accept the pain of lower valuations over a lot of structure.

Fred’s predictions come from someone who’s seen a few VC cycles. Things won’t necessarily play out just as he’s said, but his predictions are something for founders to be aware of.

I’ve had chats with a few founders in the last week about their next funding round. Many have accepted the current valuation environment but haven’t processed what impact a down round or one with lots of structure will have on the cap table and start-ups overall.

I’m of the opinion that Q1 will set the tone for 2023. If the rate of decline in public markets we saw in 2022 persists, Fred’s predictions are more likely to be accurate. If public markets are flat to slightly up, I think conditions for start-ups could be slightly better than Fred predicts.

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One of the things I’ve often heard successful investors mention as a founder trait to look for is clarity of thought. Clear thinking about the problem they’re solving and the solution they’ve built or want to build. Thoughts they can articulate clearly and concisely so others can follow along and that show they have great understanding of the topic.

For most founders, clarity of thought isn’t something that happens on the fly. It’s usually the result of taking time to truly understand a problem and thinking deeply about what you’ve learned. Deep thinking helps you organize your thoughts so you can express them clearly. And as you think about the problem more, you build conviction that you understand the problem and how to solve it based on a unique insight that others may have missed.

As I shared yesterday, paying attention to one thing at a time is important (as Charlie Munger has pointed out). Making time to think will help you do that. Making time to think is also important for founders because it leads to the clarity of thought and conviction that usually precede outsize success.