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I share what I learn each day about entrepreneurship—from a biography or my own experience. Always a 2-min read or less.
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Entrepreneurship
City for Dreamers vs. City for Hustlers
I had a conversation with an early founder who’s spent time in Atlanta’s and San Francisco’s start-up ecosystems. He’s trying to decide which will be his home base. I’m a huge advocate for Atlanta, so I was curious to hear his perspective on the two cities. He shared a variety of things, and the main thing he said stuck with me: San Francisco embraces dreamers; Atlanta embraces hustlers.
From his time in San Francisco, he learned it’s a city that respects big, outlandish visions. Even if it sounds crazy, people (investors and other founders) will support it. There’s a belief that the outlandish can become reality, have a big impact on society, and generate massive financial returns. Atlanta, he said, is a city that respects action and execution. Getting stuff done and moving things forward matter most. People prefer execution to big visions.
I’ve never heard anyone make this comparison before, and it got me thinking. I haven’t spent enough time out west to judge San Francisco, but I do know Atlanta well. I’m not sure that I agree with him. I think Atlanta embraces big-picture thinking but is also pragmatic. The pragmatism is rooted in the exits local start-ups have had. As those exits have increased in size, so have beliefs around what’s practical (for better or worse). As more founders have larger exits, I think we’ll continue to see bigger dreams embraced by the city.
Founders, Be Willing to Get Your Hands Dirty
An early-stage founder asked me for advice on handling a weird cofounder dynamic. This CEO realized that his team doesn’t respect his cofounder. Finding this odd, I dug in. I learned that the cofounder is used to a more corporate setting with resources and a team beneath him. He sees his lane as being narrow and stays squarely in it. Translation: the cofounder isn’t used to getting his hands dirty and taking on tasks he isn’t experienced in.
Early-stage companies are in constant flux and usually have only a handful of people. What needs to be done changes constantly, and there are never enough resources to get everything done. Often, everyone works on tasks outside their role—leaders included—until the company has the resources and scale to hire sufficient staff.
Early-stage founders should lead by example and be ready to get their hands dirty. Otherwise, they risk losing the respect of their team. It’s hard for your people to wrap their heads around running through a wall for you if you won’t run through one yourself.
Reflections After a Successful Raise: The Evolving Pitch Deck
I met with a founder about his successful fundraise. I was curious about what he learned from the process. Some of his learnings are to be expected; for example, realizing that to hit his goal, he needed to pitch more investors than he planned for. But he also shared something else: he didn’t crystalize his pitch (or finalize his pitch deck) until the end of his fundraise process.
This founder talked to many people who poked holes in his business from many angles. He was asked questions he’d never thought about. Most of those pitches ended in a no, but he reflected, talked with his cofounders, and made changes when necessary. While painful, the fundraising process gave him more clarity about, and confidence in, what they’re attempting to do.
A founder spends lots of time preparing a fundraising pitch deck. They often feel they’ve created a masterpiece. Many are surprised when they learn it’s just the beginning. Their masterpiece may look very different by the end of a successful fundraising.
Lower Your Personal Burn Rate to Enhance Your Optionality
One big hurdle for some aspiring founders is their lifestyle—the amount of money required to maintain it is so high that entrepreneurship isn’t a viable option. There’s an argument that every dollar that goes into the founder’s pocket reduces the resources available to scale the company. You often see founders take small salaries with large equity positions in the early years. The thought is that if the business is successful, the equity will be orders of magnitude larger than the forgone salary.
You may not have thought about it this way, but personal burn rate and optionality are correlated (for most people). The higher your personal burn rate, the lower your optionality. A high personal burn rate prevents many people from entertaining opportunities with a big upside but lower initial salary.
Anyone serious about founding a company or joining an early-stage company should keep their personal burn rate as low as possible. This doesn’t mean you shouldn’t enjoy life. Nothing’s wrong with doing one-off things that bring you joy, such as taking a trip. It does mean to be strategic about the recurring monthly payments and other monthly outflows you get accustomed to.
I like to think of a low burn rate not as limiting, but rather as not allowing past decisions to restrict your options. The lower the personal burn, the more interesting opportunities you can consider.
Do I Have a Good Reason for Doing It?
When I was younger, I made a series of decisions rooted in groupthink. Everyone else was doing it—whatever “it” was at the time—so I figured I should too. Some of those decisions proved to be painful. Upon reflection, I realized I was following the crowd instead of thinking for myself.
These days I’m very aware of this. If I find myself thinking about doing what everyone else is doing, I’ll pause and ask myself why I want to do it. If I can’t identify a reason that’s specific to my situation, I go the other way. This is difficult and sometimes isolating, but it’s served me well over the years.
I feel we’re in a period of escalating groupthink in a variety of areas. The people who think for themselves will be uncomfortable in the short to medium term but will ultimately be proven correct.
Weekly Reflection: Week One Hundred Eight
Today marks the end of my one-hundred-eighth week of working from home (mostly). Here are my takeaways from week one hundred eight:
- Energy – I thought it would take me a bit to get back in the groove after vacation. I surprised myself by jumping back in full throttle with no problems.
- Unplanned interactions – This week ended up being filled with unplanned interactions and connections with people. Although it was unexpected, it ended up being a great thing. Lots of good stuff came from those interactions.
Week one hundred eight was a high-activity week. I drew a lot of energy from talking with folks. Looking forward to more focus time next week.
It’s Only a Failure If You Didn’t Learn Anything
I caught up with an early founder yesterday. We met when he was building his first start-up. That company didn’t make it, I learned yesterday. When companies don’t survive, good founders will reflect on the experience and try to learn from it. I asked him what he learned, and he was quick to share this: “Next time, I’ll prioritize go to market too, not just product.” Translation: he focused on building a great product and struggled to get it in the hands of customers.
This founder learned a valuable lesson. Just because you build it, that doesn’t guarantee that customers will come. He didn’t give enough thought to how he would take that product to market.
Kudos to this founder for taking the time to learn from his first experience, even though it didn’t play out as he planned. His self-awareness will serve him well as he dusts himself off and starts building his second start-up. I can’t wait to see his second act.
How Do I Keep Customers on My Marketplace?
A founder building a marketplace asked for my thoughts on the risk of people connecting on the marketplace and taking transactions offline. If transactions are done outside the marketplace, his company doesn’t see revenue from the connection it facilitated.
Marketplace founders can’t stop this from happening. There will always be people who’ll do whatever is necessary to avoid paying the marketplace. You can create features and build processes to stop this behavior, but you won’t eliminate it.
The best way to mitigate it is to create so much value for both parties that they don’t want to transact outside the marketplace. And if they do, they risk losing much more than they gain in fee savings. A good example is helping supply-side participants (i.e., merchants) build their entire business around the connections made on your marketplace and making tools available that allow them to scale in ways they otherwise couldn’t.
Conversely, merchants who have thriving businesses and established tools outside the marketplace will explore the marketplace to acquire new customers and aim to take them offline.
Put differently, the best defense is to focus on maximizing value!
What Are You Afraid Of?
I was having a conversation today. It was a normal catch-up conversation. How’s life, what are you working on, etc. Toward the end he asked me, “What are you afraid of?” The question caught me off guard. I hadn’t been asked that before, and I don’t think I answered it very well in the moment.
Reflecting on it a bit today, I now have a clear idea of my answer. It forced me to ask myself some tough questions—and to answer them. I’m glad this person asked me this question. It gets to the core of self-awareness, and I think it’s a great question for founders (everyone, for that matter) to think about periodically.
So, what are you afraid of?
Great Onboarding Converted Me
I shared my thoughts on the importance of customer onboarding in previous posts (see here and here). Those posts were inspired by poor experiences related to products I was interested in purchasing. Today I had the opposite experience.
My friend wanted to meet at a particular coffee shop he’d heard about. I meet people at coffee shops regularly but never buy coffee or tea. They just haven’t been my thing, but I’m happy to support the business by grabbing a juice. I had no plans to do anything different today. Little did I know that was about to change.
As soon as we walked into this shop, we were greeted and given an impressive education on their products and the history of the company. They highlighted how they were different from competitors, gave us personalized recommendations, and allowed us to smell samples. I was impressed and intrigued. I’d never had an experience like that at a coffee shop and decided to try one of the recommended teas. My expectations were still low.
My buddy and I both were blown away when we got our drinks. He’s an entrepreneur too, so we immediately nerded out on breaking down why we thought this coffee shop would do exceptionally well. We concluded that in addition to having high-quality products, they’d done a phenomenal job of onboarding people who are new to coffee or tea. They made it easy to try something you otherwise wouldn’t through education, personalized recommendations, and sampling. All within the first minute or so of walking through the door.
This shop did an amazing job and gained two new customers in the process. I have zero desire to try tea anywhere else, but I’m looking forward to my next cup at this shop! My experience today demonstrates the power of onboarding for a business different from tech—a brick-and-mortar retail store with a physical product. Make it easy for your customers to try a great product and you’ll win!