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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
Peer Groups Aren’t for Competing
I credit the help of peers with being one of the biggest factors in my success as a founder. I’m grateful I was able to connect with other founders grappling with similar issues. We shared our experiences with each other, which helped us avoid pitfalls and go further faster.
Recently, I connected with a smart founder who could benefit from hearing other founders’ experiences. As I’ve gotten to know him, I’ve learned that it’s difficult for him to watch other people win if he isn’t winning. This mindset is one of things keeping him from stepping up from being a good founder to being a great one.
I’m a huge fan of founders helping one another via peer groups. When you participate in a peer group, it’s important to be mindful that the goal isn’t to be the “best” founder in the group, it’s to be a contributing member of the group. That means learning from and supporting one another. Learning, that is, from the experiences of smart people and applying that knowledge to your own situation. And supporting each other through the highs and lows of the entrepreneurial journey.
Peer groups are amazing, and I recommend them to anyone who can tamp down their competitiveness enough to be a supportive contributing member.
Founders, Your People Are Vital to Business Success
I’ve connected with numerous founders who have a big vision but don’t value how vital other people are to its success. They understand they’ll need help, but how they see other people is always telling. They may view others as necessary to execute specific tasks but replaceable. They treat them as an expense line item, with the compensation, equity, and responsibility they offer reflecting that mindset.
The classic example I see is a nontechnical founder building a software company. He wants to use offshore development or hire a junior developer whom he’ll manage. He thinks he needs someone to just build a product and tries to get it done as cheaply as possible. What this founder doesn’t grasp is that the software is the company. The software is a living thing that will evolve and become more complex over time. The people building it are not just an expense. They’re critical to building and maintaining a product customers will pay to use, and they should be treated as such. And there needs to be someone at the leadership level—other than the nontechnical founder—who’s responsible for this critical part of the business and incentivized by cash and equity.
When I was a founder, I learned (the hard way) that you can go further, faster with a solid team that shares in the upside.
If you’re trying to do something great, think about how you can get the best people possible around the table to help you, not how you can spend the least amount possible. That shift in mindset could be the difference maker.
Looking for Common Threads
I had a meeting with another investor recently. His journey to investor wasn’t easy. I love hearing stories like this. They show you how people are wired and who they really are. I wanted to hear his story so I could understand him better and see if I could be of assistance.
The call began normally and was cordial, but he wasn’t opening up. Then he mentioned a small detail that made me realize we might have experienced something similar earlier in life. So, I shared my experience. Sure enough, he said he’d had a similar one. From that point on, the conversation changed. We were able to relate and get to know one another via a common thread.
I appreciate this reminder that finding ways to relate to people is important. Doing so can completely change a conversation (or start it off on the right foot). More importantly, it can be a powerful tool in helping you build relationships and understand who people really are (as opposed to how they want to be perceived).
Increase in Bespoke Education
Over the last eighteen months, I’ve noticed a trend. More people are actively self-educating. They’re owning filling their knowledge gaps in areas that interest them. I’ve personally talked to people learning about personal finance, starting a nonprofit, building a real estate portfolio, and a host of other things. To be clear, I’m not saying self-education is new, but I’m seeing an increased comfort level with and desire for it.
I think that overall, this is a good trend. Knowledge is power, and people are seeking out the knowledge they feel they need to empower themselves. It will change some of their lives. Platforms—YouTube, Twitter, and others—give subject-matter experts a mode of distribution (and monetization) that’s readily accessible to the masses.
How people think about education is on the cusp of massive change. Instead of the masses accepting curriculums set without their input, we’ll start to see more people embracing a bespoke approach. Many people will take ownership of their educational paths earlier and zero in on things that interest them earlier. Lots of this education will be done via digital platforms that allow people to learn the latest thinking from people worldwide.
I’m excited about following this trend and think it could have broad impact.
Boring + Complex
Yesterday I connected with a founder friend who makes a point of mentoring and invests in early start-ups. His company is worth hundreds of millions of dollars, so he knows a thing or two about picking markets and what it takes to scale a solution. He shared his perspective on evaluating potential investments, which I found interesting.
He looks for companies that are solving boring, but complex, problems. The problem isn’t something the average person pays attention to, but it’s vital. And as mentioned, it’s complex: many nuances prevent someone from efficiently solving it manually. Think e‑commerce companies that sell nationwide having to collect sales taxes and remit and report them to various state and local agencies. Boring, critical to that company, and highly complex. Avalara, a company most people haven’t heard of, solves this sales tax problem. It’s publicly traded and as of today has a market capitalization (i.e., valuation) of $14 billion.
I like this investment thesis. I think it’s a good framework to use when evaluating companies. And I’m bullish on workflow management solutions, which aligns well with it.
I’m looking forward to working with my friend to help founders build big businesses that solve boring, complex problems.
Should I Kill or Shelve My Slow-Growing Product?
Today a founder shared his plans for his start-up. Its software product has some traction but isn’t growing quickly enough for various reasons, including timing. The founder believes the product has potential but feels he needs to pivot to work on something else for now. He wasn’t sure what to do with the product. Shut it down and it doesn’t have a chance of reaching its full potential. Keep working on it full-time and he bears an opportunity cost.
In the end, this founder decided to make the software product self-serve. Customers can do everything on their own, from signing up to canceling. The product is going on autopilot. He’ll just monitor it periodically while he pivots to build a new product. If the first product takes off, he’ll revaluate and decide whether he should step in or hire someone else to oversee it.
I didn’t much like this approach when he shared it. But as I thought about it more, I realized that I heard a similar story years ago. I was at the Mailchimp offices. One of the founders told me their origin story: a product they’d built and shelved while they worked on other things ended up becoming Mailchimp. Last week, they closed the deal to sell their “forgotten product” for $12 billion. Had they killed it instead of shelving it, their trajectory would have been very different.
The Mailchimp story is an example of the unpredictable impact of timing. Extreme, yes, but real. You never know when people will see value in what you’ve built. Sometimes it takes a little longer than you planned, and you just have to be patient and give the product time. Depending on the situation, sometimes you can work on other things while you wait for it to flower.
Entrepreneurial Impact Is Layered
One of my takeaways from my founder journey was the wide impact founders have through entrepreneurship. We had a direct impact on our customers and team members, of course. But as time went on, I began to understand our indirect impact, too. For example, the impact we had on households resonated with me. The people we employed were the main breadwinners in their households, so three or four people felt the impact of every paycheck issued. And we often heard from a customer that their vehicle (which we helped keep on the road) was critical; it was their only way to get to and from work and provide for their families. All those households, in turn, had myriad impacts on the communities they were part of. I didn’t think about impact when I started the company, but through experience I learned a lot about it—at a high level, how entrepreneurship is powerful and has the potential for massive impact.
That understanding was a big factor in my decision to become an investor. I could have taken what I’d learned from my first company and started a second. I probably could have built something many times larger than my first company in far less time. But I realized I could have a bigger impact sharing my knowledge with other founders and helping accelerate their success. The impact of many successful founders dwarfs that of one. So, I’ve been focused on supporting founders by sharing knowledge and capital.
By investing, I’ve seen entrepreneurship and the impact it can have through a different lens. I’ve started viewing entrepreneurship as something that’s layered. The company and founder are one layer—the most visible one. But other layers support them. I’m now wondering: can impact through entrepreneurship be enhanced by supporting the layers that support founders?
A Timeline Helped Me Tell My Story
I listened to a founder tell his story. He’s powered through some challenging times to get his company to where it is today. Only, when he told the story, it wasn’t as succinct as it could have been. Watching him reminded me of myself. I used to get asked about the specifics of my founder journey and didn’t always do a great job articulating them. I usually ended up sharing the details I happened to remember at the time.
One day, aspiring and early founders who wanted my help asked something about the early days of my journey. It had been over a decade, and the details were fuzzy. I responded, of course, but walked away feeling like I had given them a haphazard series of events. I wanted to help these founders as much as possible and felt like I had let them down. I realized I had to do better.
Deciding to do something about this, I settled on creating a timeline, year by year from the inception of my company. I focused on keeping it high level. Each year included five to seven bullets about the highs and lows. I included each year’s revenue so I could speak to the growth trajectory accurately. It took some time, and I had to do some digging, but the finished product was a great document.
I was super glad I created the timeline. I’d forgotten many details and milestones of my journey. The exercise sparked my memory and accurately captured the tale of my start-up.
A few weeks later, when I was asked to speak to a group of founders, I could clearly and confidently articulate my journey. The group asked tons of questions that I was able to answer by sharing my experiences.
I’m a big fan of the timeline exercise. I plan to update it annually.
If you’re a founder and not happy with how you’ve told your story, consider creating a timeline. The exercise might be just what you need to do justice to your story!
A Workflow Management Wave Is Approaching
Today I met with two founders building impressive platforms. Both are workflow management solutions focused on patient care. (You can read what I’ve already written on workflow management.) I remain bullish on these types of companies. Today was a reminder of that, and it got me thinking about the future of workflow management.
Over the next decade, we’ll see an unprecedented rate of change and disruption. Technology will drive much of it. As it develops, consumers will receive and become accustomed to better service and higher quality. To satisfy their higher expectations (which will become the norm), businesses will be forced to adapt. Efficient, consistent delivery of products or services will go from nice-to-have to essential, especially as smaller businesses try to keep up with larger competitors.
These businesses will increasingly look for help from workflow management technology. They will seek software to empower them to do things they can’t do manually but that customers expect. They’ll be looking for consistency and efficiency to meet customers’ expectations while keeping labor costs reasonable.
I foresee a wave of demand for workflow management software. If you’re a founder or aspire to be one, consider looking for opportunities for technology to make companies’ output more consistent while saving time and minimizing manpower. If you find a space that sorely needs this, you might just have come across the next billion-dollar idea.
Founders Who Exit Sometimes Want Back In
I spoke with a founder who recently sold his company. He shared the story leading up to the sale. But that wasn’t what he was most excited about. He wanted to talk about his new venture. He was approached by another founder who had built an early product and wanted feedback. As he listened, he got excited and decided he wanted to join the company as a cofounder. He’s now working hard to take his cofounder’s idea to the next level.
Founders are usually builders at heart. I’ve got a few friends who exited companies and now are building something else. They could easily sit back and relax, but that isn’t an option in their minds. They want to get back in the saddle.
Finding a cofounder is hard; it’s the biggest obstacle for many early-stage first-time founders. I’ve shared thoughts on ways to overcome this.
Today I realized that recently exited founders are a great pool of potential cofounders. They’ve got the experience and have had success. They empathize with where you are in the journey. They’re builders at heart. And most likely they have more free time than they’re used to.
If you’re an early-stage founder looking for a cofounder, consider reaching out to founders who’ve recently exited. Worst-case scenario, they don’t want to meet. Best-case scenario, you find a cofounder who’s got a track record of success!