I had a great conversation with a seasoned entrepreneur this week. Part of our chat revolved around rational decision-making. We’ve both observed exceptional entrepreneurs and investors in our social circles. Many of them have a particular trait that has contributed to their success: they can make rational decisions consistently. This doesn’t mean they lack empathy or emotion. To the contrary. But they don’t let those feelings affect their decision-making. Their decisions are based purely on reason or logic.

In a bit of experience sharing to drive the point home, this entrepreneur described how he’d made an irrational decision that cost him a few million dollars. He went on to say that had he been using sound reasoning, he likely would have made a different decision and pocketed those millions.

At the end of our chat, we agreed that consistently making rational decisions is the exception, not the norm. Those who naturally possess this trait have a superpower that helps them in making business and investing decisions.

I received an email about a small SaaS business that’s for sale. It has a few hundred thousand dollars in revenue and is profitable. I was curious how the market is valuing small companies like this, so I read through the email. Here’s what I found:

• $594k revenue (I assume trailing twelve months)
• $39k monthly recurring revenue
• Revenue has declined since purchase by new owners in 2020
• 1500+ customers
• ~$600 customer lifetime value
• 4.8% revenue churn (I’m assuming annual)
• $240k seller’s discretionary earnings (SDE)
• $750k asking price (i.e., 3.1x multiple on SDE)

If I were in the market for something like this, I’d have lots of questions for the seller, especially about the quality of the revenue and profits.

One thing that got me thinking was that this business was purchased in the last three years or so and has seen the revenue decline. I wonder about the cause—is this a case of customers seeing less value in its solution, or is it less-than-stellar management by the current owners? Not an easy question to answer until you dig into the business, but depending on the answer, the business could be a great investment opportunity or a less than ideal one.

I wonder how many small businesses have been purchased in the last three years and have been declining since then? How many have turnaround potential and will be put up for sale in the short or medium term? 

In many VC firms, someone leads each potential investment. This deal lead develops conviction about the company by learning as much as they can about it. Once they’re convinced the firm should invest, they turn their energy toward convincing others in the firm of the merits of investing.

This effort usually involves preparing an internal deal memo that details what the deal lead has learned about the company and lays out the case for an investment. To those who see them, these memos provide a rare glimpse of how VC firms evaluate a company for investment.

These deal memos are often protected work product that VC firms don’t publicize. Bessemer Venture Partners, though, has made deal memos about some of their successful investments—Yelp, LinkedIn, Pinterest, Shopify, and others—available for public viewing. These memos aren’t recent and likely have been scrubbed, but they still provide a great perspective on how Bessemer’s deal lead evaluated each company for investment.

If you’re interested in reading Bessemer’s deal memos, you can do so here.

I found a report from Carta, the equity management platform, that’s full of data and very helpful. It’s called State of Pre-Seed: Q2 2023. Carta defines “pre-seed” as “any company that has yet to raise a priced equity round.” Lots of companies begin by raising capital on convertible instruments and do priced equity rounds as they mature. Carta doesn’t explicitly say this, but I assume it also caps valuation of companies included in this report.

The report is full of useful data. In addition to high-level data, it provides granular data broken down by the two most common convertible instruments used by early-stage companies to raise: simple agreements for future equity (SAFEs) and convertible notes.

One point that stood out to me was that 52% of pre-seed companies that raised in the first half of 2023 were in California and New York. These companies were also more likely to raise more than $2.5 million in their pre-seed rounds.

The report is a great resource for anyone curious about the state of fundraising for early-stage venture capital companies in the first half of 2023. The report can be downloaded for free here.

I recently reviewed an early-stage founder’s fundraise deck. He’s raising capital for his start-up. His first start-up was shuttered when he couldn’t attract paying customers. He mentioned the first start-up to me but positioned the idea behind that business as a success because another company executed on it and is worth $10+ billion. Even though his business failed.

Most start-ups fail. Failed start-up attempts, while painful, can pique an investor’s interest. The failure itself isn’t what they focus on. What they want to know is what you learned from it and how you’ll apply that knowledge to the next attempt. If you learned valuable lessons that will increase your chances of success and speed of execution, that’s a positive founder trait to many investors.

Founders shouldn’t shy away from their failures. Instead, they should own them, share what lessons they learned from them, and articulate how those lessons increase their chances of success as a repeat founder.

I caught up with an entrepreneur who’s frustrated with a service provider. The firm handling his bookkeeping hasn’t provided him with financial statements for his multiple businesses in a few months.

I was curious how he makes decisions, knows the companies aren’t in financial trouble, and knows whether they’re making or losing money. He told me that he’s been keeping close tabs on each business’s bank accounts to get some level of comfort.

Financial statements, such as profit-and-loss statements and balance sheets, are important tools for entrepreneurs. They help you understand the financial health of your company and alert you to situations that could harm the company (e.g., a cash shortfall). Running a company without financial statements is like driving with your eyes closed. It’s dangerous. Bad things can happen if it goes on too long.

If you’re an entrepreneur, you should make sure you have relevant financial statements prepared monthly, and you should review them every month. If something doesn’t make sense, ask questions until it makes sense or is corrected. If a firm can’t consistently meet that expectation, it may be time to find one that can. Otherwise, you’re driving blind and could end up driving your company into a brick wall.

This week I was discussing an upcoming capital raise with a founder. The company has pivoted, and its latest product is resonating with prospective B2B customers. These businesses have been searching for a solution to a problem, to no avail. This founder’s solution checks all their boxes. Prospects are converting to customers relatively quickly.

Things are looking good, and the founder wants to raise venture capital. His pitch is coming together, but we talked a lot about one part of it: the market. How many customers exist for his solution? I learned that his “known” market is material but not gigantic and not growing (as far as we could tell). There’s a clear path to building a company with seven-figure annual revenue. Beyond that, not so much.  

Markets matter a lot. It’s hard to build a big business in a small market—there just aren’t enough people willing to pay for the solution. It’s equally as hard in a static or shrinking market because companies grow by taking market share from other businesses—the market is cutthroat (and likely low margin).

Venture investors understand this dynamic and spend lots of time understanding the market a start-up is operating in before they invest. If the market won’t support a large company (now or in the future), the probability of an investment being profitable for the fund goes down drastically. If they can’t see the investment turning a large profit for the fund, they probably won’t invest.

Markets matter, and founders should understand their market and its potential. If a founder can’t articulate why a market will support a large company (or multiple companies) and how their solution will win in that market, they may not be able to raise venture capital.

You learn a lot about someone who wants to be an entrepreneur when times are tough. Especially when it’s possible they could run out of cash and have to shutter their company. It’s in tough times that great entrepreneurs separate themselves from everyone else. The great ones do their best work when their backs are against the wall. They turn desperation into a superpower. They make the impossible happen.

Over the next six or so months, we’ll see which cash-strapped founders can separate themselves by making the impossible happen.

I recently had the opportunity to speak to a group of early entrepreneurs about bootstrapping. One of these founders asked about execution when you’re bootstrapping—specifically, how to execute and move the business forward when you have limited resources and limited help.

My response was simple. Early-stage founders can’t do everything they’re thinking about, especially when they’re bootstrapping. They don’t have the finances and likely don’t have the manpower. Figure out what the most important next milestone is and what actions get you closer to it. Focus intensely on those actions. Don’t worry about the other stuff. Said differently, figure out the 20% of activities that will make 80% of the difference in getting you to your next milestone.

Focus is important when you’re an early-stage company. You have tons of balls in the air, and you’re adding more all the time. Many early-stage founders (myself included) try to keep juggling all those balls, but it’s just not possible. You don’t have enough hands. It’s better to figure out which of the balls matter most (given your stage). Keep the critical balls in the air and let the others drop (for now). 

Homing in on what’s most important is easier said than done, but it can be the difference between success and failure for early-stage companies (especially when they’re bootstrapped).

OnlyFans is a social media company that’s surged in popularity since the pandemic. The company has a less-than-stellar reputation because of the type of content creators post on the site. I’ve never used the site and don’t know a lot about it, but I read an article about the financials that caught my attention.

The parent company, Fenix International Limited, is based in the UK, so its financial statements are public. I looked at its latest financial report covering 2022 and noted the following:

• Creators on the platform grew 47% to 2.16 million
• Fans (i.e., users) on the platform grew 27% to 187.9 million
• $1.09 billion in total annual revenue
• ~67% of annual revenue is generated in the US
• ~48% of revenue is subscription
• ~52% of revenue is transactional (take rates from purchases)
• Net profit (after taxes) of ~37% or $403 million
• Dividend of $338 million paid in 2022
• Dividend of $310 million paid in 2021

Bloomberg says the company is owned by a single individual, to whom all dividends are paid.

Again, I don’t know anything about the platform and haven’t used it, but its financial performance is something to take note of. The revenue, net profit, and dividend figures surprised me.