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.

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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.

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?

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!

Today marks the end of my eighty-fourth week of working from home (mostly). Here are my takeaways from week eighty-four:

• Impact – I’m still thinking about this a lot (and having great conversations about it). I have some ideas for having an impact on founders and may start to test one pretty soon. Looking forward to learning.
• Directionally accurate – I’m naturally wired to have a destination in mind that I’m aiming for. Over time, I’ve learned that I can take action without a clear destination—I just need to lift my head periodically to confirm I’m still headed in the right direction. This week reinforced this.  
• World Series win – The Atlanta Braves won the World Series for the first time in over twenty years. This is a big win for the city and puts it on outsiders’ radar screens. Sports have a way of uniting people, and I’m excited to see how this win will affect Atlanta.  

Week eighty-four was positive. I was productive and reenergized. Looking forward to repeating this next week.

A few years back, I was asked to attend an event. I knew the organizer and he asked for my support. I was busy at the time and wasn’t sure I’d have the bandwidth to attend. I was on the fence until the last minute but ended up going. At the event, I met someone who’s now a good friend—and who introduced me to other people who’ve had a big impact on me.

That one event has had a lasting impact on me in ways I never would’ve imagined. It and other situations I encountered as a founder have shown me how powerful serendipity can be. Just being in the right place at the right time can make a world of difference.

The last eighteen months have made serendipitous interactions difficult. It’s hard to have random interactions when everything is scheduled via Zoom. I enjoy the efficiency of video calls, but I do miss those chance encounters.

I’m not sure what the future holds or what the future of work looks like, but I’m looking forward to a little more serendipity in 2022.

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.

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!

Met with a friend today who runs his own company. Seven years ago, he told me he was thinking of making the leap. He’d had a stable job for many years, though, and wasn’t sure how he or his family would weather the ups and downs of entrepreneurship. But he was passionate about the industry. In the end he decided to jump. His wife was supportive (given that certain conditions were met beforehand), and they lived a modest lifestyle. He started the business on nights and weekends. After getting some traction, he went full-time with his wife’s blessing.  

Fast forward to today. He has a booming company that’s growing fast and a big vision. He plans to build a massive company. At the moment, he’s working through how to scale operations while maintaining the quality his customers have come to expect. We talked about how software could be what’s missing. I’m planning to connect him with some software founders who are building products for his industry.

I’m glad my friend bet on himself and that things are working out. I look forward to following his journey and have no doubt that his vision will become his reality!