Interview with Brad Feld – Books, Investments, Depression and Productivity

About a decade ago, when I was fundraising for WhoAPI, I was looking for investors who could help us with advice, connections and funding. As I shared in a blog post back then, investors ask tough questions! My connections in the domain name industry (I did the research for .me registry), led me to a startup with a .me domain name. Foundry Group invested in attachments.me (no longer active), and as you will find out in the interview below Foundry Group made several investments in the email niche. After meeting with Ben Coe, the founder of attachments.me in San Francisco, he introduced me to Jason Mendelson, whom I ended up interviewing. Jason is no longer with the Foundry Group, and I can’t stop myself from interviewing, so I reached out to Brad Feld this time.

I am no longer fundraising, but since Mr. Feld has shared a lot about mental health and depression, which is particularly common with startup founders. After the pandemic, it seems that many are fighting this growing issue. Even though I haven’t had any serious problems with depression one family member has and I’ve been exposed to the dangers of that illness. Furthermore, Foundry Group have tremendous experience with investing in API companies such as Sendgrid and FullContact. Since I’ve interviewed both of these company’s founders, interviewing someone from Foundry Group seemed like a full circle to that story.

Goran Duskic: In your book “Startup Life,” you recommended one of my favorite books, Power of Habit, by Charles Duhigg. I think you intended to encourage your readers to focus on doing the small things. I believe that small habits are, to use one of my favorite quotes by Jim Rohn, “do what you can, do the best you can.” What are your habits and “small things” now that you are Brad Feld that everyone knows? More importantly, do you remember what were your habits and “small things” when you founded your first company Feld technologies? What does your typical day look like, and is there an area where you focus twice as much as the next guy?

Brad Feld: My dynamics around habits have changed a lot over the years. I used to be obsessed with certain things done like Inbox Zero and crossing everything off my to-do list every day. I no longer care about any of that. When I want to learn something or do something new, I spend time on it every day until I decide I’m not interested anymore or it’s become embedded within my routine. My typical day has also changed a lot. For many years, I felt oppressed by my schedule, which I called “the wall of blue.”

Web on “the wall of blue”.

Now, I only schedule things on Tuesday, Wednesday, and Thursday between 11 am and 5 pm. My Mondays have some recurring stuff, but other than that, I try to let the time be fluid. I also try to have a “no scheduled week” each month where there is little to nothing scheduled so I can work on whatever I want, which includes plenty of things that come up and need attention but don’t require scheduling in advance. I’ve always been an early riser, so I get up around 6 am, spend 30 minutes having “morning coffee” with Amy, and then go for a run most days. I finish up around 6 pm and either read a book or watch TV with Amy and am in bed around 9 pm.

Goran Duskic: This is congruent to what you wrote in your book, about rhythm and how there are myths you can work like a machine and sacrifice everything else in the company’s service. One caveat to that would be that you break down at some point. I was guilty of that, and as I mentioned in my ebook, I ended up with mononucleosis during my acceleration period at 500 Startups. At one point, I was fundraising out of bed. On the other hand, some entrepreneurs understand this rhythm. As Bart Lorang shared in an interview, FullContact offers their employees the “Paid PAID vacation” so that everyone can complete the regular cycle.

How can startup founders be more effective at fundraising and other similar excruciating startup experiences without falling into the trap of “6-week common cold”, “burnout,” and other stress-related results? We’ve seen recent articles of significant VC funds and accelerators posting warning signs of the coming doomsday.

Brad Feld: I used to have daily, weekly, monthly, quarterly, and annual rhythms. I stopped doing that in 2013 when I had a six-month depressive episode and decided to change how I was doing many things. I started paying a lot of attention to what caused me anxiety and fatigue. I stopped drinking alcohol (I’ve never done drugs). I started getting at least eight hours of sleep each night. I stopped traveling or at least minimized it. I realized that crowded group events were no longer enjoyable for me, and I shifted all my social activities to smaller groups (with one other person or with Amy and another couple.)

I got much more aggressive about protecting my weekend time from meetings and work time, so I could have a lot of space and time to take care of myself and be with Amy. We continued to make life dinner once a month (we just had one last night), and I take a week off the grid every quarter. By studying myself and experimenting, I learned what environmental factors were the root cause of my anxiety, depression, and fatigue. Then, I changed things to improve the context and environment. I don’t think there are generic answers.

Everyone has to figure this out for themselves, given their physiological makeup, life configuration and constraints, and fundamental goals and desires.

Goran Duskic: What do you mean by that?

Brad Feld: View yourself and your context as the laboratory and experiment. Systematically try different things, measure your responses, and iterate. Make adjustments. Experiment some more.

Goran Duskic: What impact have you seen on startups with founders having large families or problems with personal finance? The reason why I put those two together is that they both don’t have absolutely anything to do with a startup but can tremendously impact the way a startup founder is performing. For example, using the money for diapers instead of R&D. I know it sounds cold, but these decisions are the harsh reality of life. Money and focus on diapers or building a company. How do you deal with that?

Brad Feld: It’s extremely challenging, and I don’t think there are easy answers. However, finding a peer group and acknowledging that it’s a massive constraint and stressor for many entrepreneurs can be helpful. An example of an entrepreneur who faces these challenges taking a leadership role is James Oliver with his ParentPreneur Foundation.

Goran Duskic: Speaking of different struggles that entrepreneurs face, there was an interview with Rand Fishkin where he briefly talked about his struggles with depression. He also mentioned your support in those tough times. I always ask successful entrepreneurs (as I asked Mitch Wainer, co-founder of DigitalOcean) about getting the motivation and inspiration to get up in the morning, even when they have achieved what most are striving to achieve. I am going to ask you a slightly different question. How do you get up in the morning, regardless of your level of success, when you don’t see the point of getting up at all?

Brad Feld: When I’m not depressed, I love getting up in the morning. That’s been especially true for the last few years as Amy and I spent 30 minutes together first thing, having coffee together and talking about the day ahead. When I’m tired or when I’m struggling, I just get up, do what I need to do, and can manage it for about eight hours until I get tired. Fortunately, I haven’t been depressed or tired for several years, so the mornings are mostly just happy moments.

Goran Duskic: Throughout the interview, you mentioned Amy a lot, so I think it’s safe to say she’s essential to you. I also live with a great partner that completes me. Please help me make the connection for somebody reading this interview on a highly technical website. APIs and romantic relationships don’t make sense from afar, but having support is very important. Should someone focus more on finding somebody special instead of coding?

Brad Feld: It’s been essential to my life, but I think this is a highly individualized decision.

Goran Duskic: I’ve learned from interviewing Isaac Saldana that Foundry Group invested in startup Sendgrid. Can you tell me how the story went from your perspective? What was your gut feeling in the first 5 minutes, and what’s your gut feeling now? Were they still called SMTPAPI.com back then, or were they Sendgrid at that point?

Brad Feld: We met Isaac when he and his co-founders went through the Techstars Boulder program. My partner Ryan McIntyre and I have made many email investments and liked Isaac from the beginning. Ryan was a formal mentor, and I endlessly teased Isaac about the name, calling it “Smitpappy” to encourage him to change it to something less nerdy. While we didn’t lead the round for SendGrid when they finished Techstars, we stayed close, and pre-emptively led financing after another company approached them about buying them early in their journey. I’m glad Isaac and his co-founders let us invest – it was an outstanding experience.

Recommended reading for startup entrepreneurs

Recommended reading for startup entrepreneurs

Goran Duskic: We started this interview with books, and you are a big reader, so let’s also end with a book. What’s the last book you read? Can you recommend any books to entrepreneurs working on getting to the next level?

Brad Feld: You can find the list of all books I’ve read on my Goodreads page in reverse chronological order. I’m reading Kim Stanley Robinson’s The Ministry for the Future, which is spectacular. One of my early books, Do More Faster: Techstars Lessons to Accelerate Your Startup, is still a good one for early-stage entrepreneurs looking to make progress.