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Keep in Mind Fit Matters Too

Founders looking for capital will likely talk to a lot of investors and hear no repeatedly before they hear yes. It’s a frustrating process. Today I was talking with a founder friend about finding the right investor. We discussed the importance of fit.

Founders have an objective they’re trying to achieve. They need capital, start-up knowledge, and relationships to execute and turn their vision into reality. The investors that can help them achieve this objective are the best fit. Founders are (or should be) evaluating investors for fit, but what they often don’t realize is that this is happening on the other side of the table too.

Investors, like founders, have objectives. They’re looking for opportunities that are the best fit with their objectives. Investors’ objectives vary. They probably include potential financial return, but they may also include other variables. For instance, an investor may want to fund a start-up with a specific approach to solving a problem. Or invest in certain types of solutions (e.g., software) and not others. Or give back to the community as well as make money (do good while doing well). Whatever their objectives are will play into their decision-making process. This means you could be a great founder with a great idea, but the opportunity might not be a fit with a given investor’s objectives.

Good relationships are mutually beneficial. Founders should be mindful of this when evaluating investors (or any partner for that matter). Clearly articulate what your objectives are—but understand the objectives of the other party too. The goal is to find fit: alignment of the objectives of both parties, even if they differ. When there’s a fit, the relationship will be mutually beneficial.

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What You Don’t Know Can Hurt You

I spoke with a founder who’s smart, and the solution he’s looking to build could bring real value to customers. He wants to raise capital but isn’t familiar with the venture capital process and doesn’t know anyone who’s been through it. Recognizing his knowledge gap, he wanted some pointers.

This founder’s approach is a good one. Try to fill your gaps and build a network of people who are knowledgeable about raising venture capital before you begin trying to do it. I suggest getting as many perspectives as possible. Socialize your idea with investors and ask for feedback. During those chats, you can ask them how their firms’ investment processes work and what they’re seeing in the market. Founders are a great source of knowledge too. They can give you their takes on current market dynamics and valuable insights gleaned from their experiences.

Maybe you don’t have physical proximity to any of these people, but you always have digital proximity. Blog posts, Twitter threads, YouTube videos—investors and founders have put out a lot of content about fundraising.

In the end, you want to avoid being in a situation where you’re at a disadvantage with respect to information or knowledge about the process and current market when you start raising. Not knowing can have a big impact on the outcome of your fundraising.

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Thoughts on Bootstrapping vs. Venture Capital

I spoke with a buddy today who asked me for my thoughts on raising capital for his business versus bootstrapping. I shared the lessons I learned from bootstrapping my own start-up and from investing as a venture capitalist:

  • Market size – It’s important to understand the size of the market you’re going after. If it’s a small market, raising capital is less likely to make sense. If it’s a large one, then raising capital can make sense, depending on other factors.
  • Destination – Once you understand how big the market is, you can determine how much of it you want to capture. CCAW’s market was $40 billion. I figured we could realistically capture 1% of it and build a $400 million company. Sadly, I didn’t think about this early enough in my entrepreneurial journey.
  • Speed of execution – Once you know how big a company you want to build, you can think about the time frame for achieving your goal. The faster you want to execute, the more resources you’ll need. If you believe you’re facing a closing window of opportunity, you may want to execute as fast possible.
  • Team – Given the speed with which you want to execute, who do you need on your team? Unsurprisingly, the faster you want to execute, the more people you’ll need.
  • Runway – Consistent execution is important. You’ll want to make sure you have enough financial runway (i.e., cash) to consistently execute on your plan at the speed you envision. If you’re executing at a slow to moderate pace, bootstrapping may suffice. It’s more challenging (though not impossible) to provide ample runway for rapid execution if you’re bootstrapping.
  • Accountability – The bootstrapping approach usually means the founder isn’t accountable to anyone. If you raise capital from others, it comes with an enhanced level of accountability. In my experience, most people need accountability—but no one wants it.

How to capitalize a new or existing business is situational. This is one of many decisions a founder has to make. There’s no right or wrong answer in the abstract—only the right answer for your situation.

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Considerations When You’re Funding Your Company

I chatted with a founder today about my experience bootstrapping my company. We discussed the pros and cons of various ways of capitalizing a company and factors to consider. Here are the main takeaways:

  • Talent – If you’re going after a big opportunity, you can’t do it by yourself. You need a team. You want to find the best and brightest people you can. These A players usually want to be compensated for their talents. They may accept equity and cash compensation, so you may be able to go a little lower on salary. But you don’t want them looking over their shoulder for the next opportunity. You need ample capital to pay people what they’re worth.
  • Runway – When you’re executing a plan, it takes time to see a return on your efforts. You want to give yourself enough breathing room for your hard work to start paying off.
  • Strategic thinking – When founders aren’t focused on day-to-day survival, it’s possible for them to think strategically about the business. And founders should be thinking long term about the business—which they can do only if they’re not trying to figure out how to pay this week’s payroll.

There isn’t a right or wrong way to capitalize and grow a company, but these are important considerations for founders. Bootstrapping and raising investor capital are common approaches, but there are others. Pick the one that’s right for you and that sets you up for success.

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Atlanta’s Latest Decacorn: Mailchimp

Today Intuit confirmed that it’s acquiring Mailchimp for $12 billion. Mailchimp started by building software for other clients. Then it built a product to simplify marketing via email, pivoting the entire company around offering it to small and midsize businesses. Since then, the product has expanded into other areas, but it’s still focused on empowering SMBs.

Congrats to the Mailchimp team for a huge win. Atlanta has known this company is something special for a long time. Today, that was demonstrated to the world in a big way!

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Distribution Is Changing the Banking Landscape

I’ve shared a few of my views on Apple’s potential to be a consumer bank and how consumer lending is heating up. Yesterday I had the opportunity to chat with someone who’s worked at one of the largest US banks for over twenty years. Our conversation was social, but I couldn’t resist sharing my views and getting his take on where banking is headed. Our chat was enlightening. I learned a great deal about the inner workings of the bank, how the largest banks view Atlanta as a strategic city and are expanding rapidly, and how this has led to a hyper competitive Atlanta market for bankers, with salaries rapidly increasing.

One of the biggest takeaways was that what matters to consumers in a banking relationship is changing fast. Historically, large banks won because of their branch networks. The more branches, the better. Consumers knew that wherever they were, they could find a branch and get whatever help they needed. The branches were banking’s version of distribution. The branches were a core part of how the products and services the bank offered reached their customers. Establishing a network of brick-and-mortar branches was costly and time consuming, so the largest players had moats giving them defensible competitive advantages.

Now, consumers are rapidly shifting from in-person banking interactions to digital banking interactions. You don’t need to go to the bank to deposit a check or get a loan. You can do many tasks electronically via a mobile app or website. Because of this shift, consumers evaluate banks differently. Consumers care less about a network of branches because they don’t need to visit branches. They care more about digital tools. They want the best and easiest-to-use technology.

This banker was telling me that digital distribution is changing the banking world. The large banks that previously had the best distribution because of their branches are seeing their moats erode quickly. The companies that offer the best digital experiences are winning.

How companies get their solutions in customers’ hands matters a lot. Said another way, distribution matters a lot. The digitization of distribution will drastically change banking. Apple, Square, and other companies will compete for banking relationships like never before.

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Early Start-up Employee Turned Fund Manager

I had a great conversation with another investor who’s had an interesting journey. He worked in corporate America learning hard skills out of undergrad. Then he joined a start-up as an early employee. His skills helped the start-up minimize painful learnings and release a superior product in less time. Equity was part of his compensation package. Eventually, he made his way to venture capital and learned how to invest in early-stage companies. The start-up he’d worked at years before went public, and his early equity turned into a significant financial windfall. He began doing personal angel investments, and now he’s planning to raise a fund to help founders in his area of expertise.  

He understands start-up life and entrepreneurship from various perspectives. Now he’s taking what he’s learned and the wealth he has amassed from his journey and using them to help more founders become successful.

People like this have a huge impact on start-up ecosystems. The combination of capital, operator knowledge, and relationships can be game-changing for early founders. I look forward to watching this investor transition to fund manager. I’m sure he and his team will move his space forward!

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Big Boys Going after Consumer Lending

Earlier this week, I shared my thoughts on consumer lending heating up. It’s a large and growing market that’s big enough for multiple winners and hasn’t kept up with changing consumer behavior. The market opportunity could move the needle for any company, even a juggernaut like Apple.

Today it was reported that Apple is partnering with Affirm to offer a buy-now-pay-later option for Apple devices purchase in Canada. This is yet another big announcement in the consumer lending space within a short time. Apple and Square are making big bets on it. (Affirm was already in the space.)

I figured consumer lending would be strategically important and change quickly, and it appears to be changing even faster than I thought. Change is generally good—I’m a fan of it. Especially when it helps solve pain points for consumers in a better way. I can’t wait to see how this space is revolutionized by these new entrants.

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Consumer Lending Is Heating Up

Last month I shared my thoughts on how I could see Apple as the go-to consumer bank in the future. Since then, it’s been reported that Apple has partnered with Goldman Sachs to offer a buy-now-pay-later option for products purchased via Apple Pay on Apple devices. Today it was reported that Square is acquiring an Australian pay-later company for $29 billion. This announcement caught me off guard and got me thinking.

Consumer lending is a large and growing market. It plays a key role in the overall economy, so it’s big enough to move the needle for a huge company like Apple. And the market is large enough for there to be multiple winners. It’s not on the cutting edge—it hasn’t kept up with other changes in consumer behavior. Considering these and other factors, the moves by Apple and Square make perfect sense. I suspect they won’t be alone—we’ll see more companies entering this space.

I think consumer lending is about to change rapidly. I’m excited to see new entrants in the space and can’t wait to see what direction this goes in.

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Preparing Financially for Entrepreneurship

An aspiring founder asked what I did financially to prepare for entrepreneurship and what I recommend. I started my company over a decade ago. I wasn’t far removed from college, and the world was a different place in general (inflation is real). Here are a few things I thought about that others may find helpful:

  • Reduce fixed expenses – Your personal cash flow (i.e., salary) will likely decrease during your early years as a start-up founder. Reducing your fixed expenses (recurring fixed monthly payments) will give you more flexibility. You want to be able to focus on the company. But you don’t want to reduce them to the point where life is miserable, either.
  • Reduce debt – Eliminating or reducing unnecessary debt is easier said than done. But if you’re fortunate enough to be in a position to do it, it will help diminish financial stress and lower debt repayments or remove them from your fix expenses altogether.
  • Increase savings – Start-ups are hard and unpredictable. It’s not unheard-of for founders to take small salaries, go without a salary, or inject personal capital into the company when times are tough. Savings are a financial cushion that helps you weather the early years. If you can, increase your savings before you start your company.
  • Get buy-in from loved ones – If others are affected by your entrepreneurial decision (e.g., family or a significant other), being on the same page is important. Discuss how entrepreneurship will affect the household (including finances). It’s important for everyone to have an idea of what the journey will look like and buy in.
  • Consider a Roth IRA – If you’re eligible, consider opening a Roth IRA (you can fund it later). This is a great retirement vehicle in the traditional sense and also an interesting tool that founders can strategically use to invest or hold alternative investments (e.g., private company shares).
  • Eat in – We eat three meals a day. Eating out is expensive, so eating in can improve your personal cash flow quite a bit.

These are just a few things that aspiring founders can consider doing before they start their company. Everyone’s situation is different, so some of these won’t be feasible for everyone. Still, they’re good things to be aware of and think about. Building a business is hard. Minimizing stress in other areas in your life can help a lot.

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