The Many and Wondrous Forms of a Builder’s Ambition

A conversation with Brett Kopf, founder of Remind and Omella

Lately I’ve been struck by the many and wondrous ways to be a builder. For instance, as I wrote in Being entrepreneurial about entrepreneurship:

For some people, in some circumstances, [being entrepreneurial about one’s life] might mean taking a job within a well-established institution like McKinsey; for others it might mean going outside established institutions and starting something new, with or without investor funding; for others it might mean going to school, or taking time off to raise kids, or waiting tables to make ends meet while learning to code or auditioning for acting roles or working on a novel. No one is ultimately more qualified than you to judge what particular path to take, or what advice to follow, or what institutions to accept or reject. Just stay awake to the fact that it’s your life on this earth you are building—and then choose accordingly.

And as I further elaborated in Your flaws matter less than you think:

Keep in mind that the concept of a “flourishing, fully-lived life” is abstract. Its universal demands are at the level of things like the need for self-honesty and the exercise of our agency. Beyond these fundamentals, thriving does not have one specific look. A life devoted to the single-minded pursuit of a passion at significant cost to personal relationships or physical health (a la Marie Curie, for example) may be just as “perfect” as a quiet life largely centered on cultivating strong, healthy family relationships, or a life of bustling variety, or any number of other sorts of lives… By contrast, one of the failure modes that precludes a “perfect” life is the passive (i.e. non-agential) adherence to some sterile, generic template of a “good life,” instead of custom-building a life that fully leverages your own inimitable mix of affordances and constraints and idiosyncratic conditions for thriving. 

In addition to this between-person variability in the lives builders build, I’ve been reflecting a lot on the within-person variability to which impressive and interesting people are often prone. Being truly ambitious about your life means you’re highly selective about where you channel your ambition at a given point in time—and you allow this to change according to what your fully-lived life requires.

Thinking back on my Founder’s Mindset podcast conversation last year with the exceptionally self-reflective Brett Kopf, co-founder of Remind.com and Omella, I keep remembering new ways his personal story embodies this theme. Brett’s motivations for starting his two companies, the approach he has taken to building and growing each one, the manner in which each one slots into and intersects with his personal life—these two epochs of his founder journey couldn’t be more different, yet both are profoundly inspiring and both bear his unmistakable signature.

Here are some illustrative excerpts, with the full transcript below (for paid subscribers):

Brett 1.0: serving 30 million users, going to therapy, watching dad die

The first part of the conversation focused on 22-year-old Brett’s dizzying experience of building and growing Remind.com—a messaging platform that 80% of U.S. public school teachers now use to communicate with their students.

For some cultural/economic context, Brett and his brother David co-founded the company in 2011, when messaging was new and venture capital funds were flowing into high-growth, high-risk tech startups.

And grow they did: Bret recalls “adding 200,000 to 350,000 users a day, 85% of which we would retain. Faster than Facebook, WhatsApp, at the time of growth.”

What motivated the young Brett to build Remind.com?

I was diagnosed with a slew of learning disabilities when I was a kid. And I pretty much spend the next, call it 16 to 17 years in my life, feeling not smart in school. And that was mostly because the structure and the system that I grew up in - and I went to a wonderful public school—it just wasn't fit for me. I was just a bit different. And I would be taken out of exams and classes, and I would have extra time, and I would have a special teacher to help me on things, and then the undercurrent—the emotion of what that made me feel—was not smart. Now I feel smart, now I'm very confident with who I am and who I'm not as an adult, but for a very long time it was difficult to figure out. And so that sort of energy of feeling not smart propelled me to start my first company.

Why specifically a messaging platform for teachers?

So tactically, Remind is like Slack for education. I wanted it because I had this teacher that totally changed my life. She sent me—well, what she really did was like she cared about me a lot, but I noticed that she was struggling to communicate with our students. And so I tried to solve a problem for her. And Remind then became very big… and I learned a lot about the world just being thrown into the deep end.

What were some of the things he learned?

…Emotionally, I wanted to prove so badly to the world that I wanted to build something that was highly impactful on a very large scale, that I would have this energy or this lifeforce inside me that would make me work my rear end off… I would work really, really hard, and I also wouldn't prioritize things that mattered. Now, what matters to me now is my emotional and physical health, my family, my nuclear family, and then my company, in that order. But when you would have asked me when I was 22, or 21, it wouldn't have been that, probably because I was young and naive. And I just sort of hadn't lived enough and been through experiences. And so because I didn't feel smart, there was this emotional propellant to want me to prove to the world—aka probably my father, who has since passed—but, like, prove to him that I could be something, and live up to his expectations. At the time, I had no idea that I was doing that, like, that I had that drive, though, because I wasn't aware of that.

How did he learn them?

I first started seeing a therapist… when I was living in San Francisco building my first company…. His name was Garrik, he was amazing, and one of the things that I felt like he was really helpful with was being a very safe, transparent, reflective mirror to my conscious and unconscious mind. And one of the things that he always explained to me is like, it's really hard to figure out why you are the way you are, and do things that you do.

At the time my dad was dying... [right] at the time of [rapid company] growth. It was crazy, [we] raised a ton of money, whatever, all of that stuff. So there was a huge amount of pressure, self-induced, but also just to perform in the world, especially because our customers needed it. And there [were] all these personal things that were happening in my life at the time, too. So, my dad had Parkinson's, and he was sort of on his downfall…. And for me, it was helpful to categorize the big problems in my life [in therapy]. One problem was like trying to reconcile the death of my dad. No, he wasn't dead at the time, but he was on that path. The other problem was trying to decide if I was ready to get married to my now wife, which thank God I did, but that was really hard. But I didn't know, which he helped me figure out, that my dad dying and kind of coming to terms with that was sort of a mental block to me even getting to the point that I can be ready to take that next step with my wife…. [H]e helped me structure those things and understand the realness of them. Like, you know… when the company was growing so fast, it was hard to even take the time to consciously say like, "well, your dad's dying right now”… And so he gave me that space, that structured space and time to do that. And we would talk about those things and understand how it was making me feel.”

What was it like to process all this while scaling to 30 million active users?

When like my dad had Parkinson's, there got to be a point where he could hardly move, he could blink his eyes as a yes or no. It's like the worst torture that you can imagine for a human, and for a loved one to see. And to compartmentalize and decouple the things that were happening in career life versus personal life is brutal, especially for a 22 year old… As an entrepreneur—look we have a lot of customers who did really care about me as a human, but at the end of the day, it's not their responsibility to necessarily care that I have this very real personal thing happening. When they send a text message, and they relied on my service and Remind to do something, and it had to do that thing. That's just the reality of it. And so [I’m sharing this] because there's like the surface level as an entrepreneur, what you're doing building something for the customer, and you have employees - but then there's the personal undercurrent of all the things happening in your life good, bad, or ugly, which are inevitable - and everyone goes through something - it's very difficult to manage both of those. And they are both true. Meaning I had to somewhat handle my personal life, and you have to execute at a very high level for what was demanded of me for my company.

Does he regret how hard he worked and how little time he reserved for family at the time?

No… I think that, given the skills that I had at that point (and I have more skills now because I'm more experienced), I don't think I had the emotional or physical capacity in the day to do other stuff.

Where does that additional capacity come from?

I think there's probably a mixture of time and experience. And like, I've just seen a lot of things, and you have a lot of shots on goal. And then my son—like when I had my son—he's almost two years old—for me it put a new perspective on what matters and why.

Brett 2.0: Building wisdom, reaping joy

Then, after Rewind.com had grown huge and Brett’s father had died, he took a step back and consciously re-prioritized his life:

I stepped out of a day to day operating role in my first company, I took a year off and I traveled with my wife for some of that time, and I kind of reevaluated what the heck just happened. And then what qualifies [as] a happy fulfilled life for me—I say me because everyone's different. And what I decided was thematically, there is my physical, emotional health, the relationship I have with my very close family, specifically providing for my wife, and with my son, and my dog. And then you know, my mom, my brother, the close people, and then it's the company. But I reprioritized my life out of all of that. And I could not have done that [during the Remind.com epoch]. I just wasn't mature enough.

So what motivates him now?

Well, I now prioritize everything that I mentioned. It's like health, family, then company; everything is revolving around that. And I don't care what external figure wants me to be another way, I just don't care. External figure could be a VC or like the press, I just don't care. Like, because I care more about providing or being with my son, than I would be on the cover of Forbes. I cared about being on the cover of Forbes when I was 21, I don't give a sh*t now, excuse the french. Unless it helps us acquire a bunch more customers, because that's what we're focused on now….

Let me be clear on that: I want to build Omella, I want it to be very large and very impactful, someday as big as Remind is. I do want that. And I get up every morning at 4:30 in the morning to grind a few hours in the morning before my kid wakes up so I can help him get ready. And then I go back to work. And so I still work very hard. But I'm not willing to sacrifice. So what that means is, probably at like four or five o'clock I stop working and I spend the next four or five hours with him. It also means that I spend one hour during the day exercising.

What does this mean for his approach to the business?

One from just a pure business standpoint is I want to have a business with strong, what you call basic business fundamentals and clear unit economics, which always come back to, do your customers come back? Do you have healthy retention? Do you have a high margin? Do you have high engagement? Are you growing in a healthy manner? Meaning are you making more money than you're spending, and having a good business model so you could be running the company forever? Like, that part's really important to me. Part of the reason is because with Remind we didn't charge for a long time, I think for that company it was right, just because we were growing so quickly. But I [now] want to build a company, and before it was maybe more of just a product.

And then there's the value systems of how we build it…. right now it's kind of a scary time, there's layoffs happening right and left, and valuations are getting slashed by 80%, but I think some of it’s good because it gets back to truth and clear fundamentals. And it's like, put up or shut up, if you're not going to build something that's valuable that a customer wants, probably the company's gonna die. And it won't be the end of the world, and you're gonna learn from it, and maybe you'll build something else, or maybe join someone else… For us, at Omella, our economics are clear. We make money on every transaction, but now it's like, how do we get to break-even profitability as fast as thoughtfully possible.”

What’s remained constant about his motivations as a founder, and what’s changed with experience?

[What I love is] talking to customers and deeply caring about them and wanting to help them, [in] this niche that is very big that no one knows about… I love that more than anything [and have loved it since Remind.com]. But then there's a set of value systems that apply that I believe are right, that [are] different from the old version of me, version one. Which, maybe if you went to business school—which I didn't, I studied agriculture and I nearly dropped out of school—they would teach me, but it's like clear fundamentals on what is a good healthy business, and wanting to do it for the right [reasons].

So let me give you an example. For this new company, Omella, we raised like, I don't know, four or five million bucks. Every single investor that came in, I said this will not be an overnight success, you have to be with us for like 10 years. You should not expect liquidity for 10 years. And if you want liquidity faster, please don't invest in the company. By the way, we don't need your money. And setting those expectations upfront was really important. Because we only wanted people who weren't going to be knocking on my door every day. A lot of this confidence, by the way, comes from just doing it a few times and knowing what I believe to be right and true in the world. And knowing that if I'm wrong, I'm gonna admit it, and I took a shot at gold and I tried.

What does he still struggle with?

…I have my career identity where I want to build something really impactful, and I have to work a lot…. And I think the company needs it. And also I want to spend time with my son and my wife, and I want to exercise and do the things I want… And unfortunately, one thing that scares me a bit is that I don't know too many public figures - and maybe this is just because the ones that aren't public are busy with their personal life or working—that have figured out both, where financially the things that they have built in the world are very impactful, and they have a very intentional, good personal life. Usually it's like crazy workaholics that are really not good personal life. And I don't want that.

….The [other] thing that I'm not necessarily as good at is managing my emotional state…. I was talking about it with my wife this week, it's like ah man, it's either I'm working, and I wonder what my son's doing right now, or I want to be with him, or I need to exercise. Or when I'm exercising—unless I'm playing basketball, because then my mind turns off, which is great—but if I'm lifting weights, it's like, “oh gosh, I have to answer this support ticket." So it's still hard; I'm still conflicted on both, because at the end of the day, I want to build something that's very big and impactful. Just for me personally, I'm not okay just building something that is sort of average, because I see this vision and I want to help these customers, I really do, I really want to have that impact and help them.

What are his overall takeaways for anyone wanting to build (a company or a life)?

[W]hen you build a startup it's really simple, you talk to customers a lot, you solve a simple problem for them, and you build a product that solves their problem, and you iterate rigorously. I spoke to 500 customers before we wrote a line of code. And so like that general framework is how I build all my companies. There's a lot that falls underneath that, but that's it. Just like talk to customers. Listen with two ears and one mouth, build a simple product, and solve a problem. That's like the framework in which I start the company.

The personal stuff, that's super hard. I don't know if I have any [takeaways], other than like, know thyself. I remember my dad, when he was actually passing, which I could not literally hear him. Well, literally I could but metaphorically, I couldn't. Where he said, "you know, Brett… all work and no play makes Johnny a dull boy.” …And all I hear was like, "yeah yeah Dad, whatever, like, I gotta grind, I gotta grind, I gotta grind." And it's like, oh wow, I'm 36 now… and it's like, oh, you know, you kind of see 50, and kind of see 75 and 100, and it goes really fast. And once you have kids… you know how fast it goes. And he had an interesting point there.

Now, at the time I couldn't do anything with that, because I was so focused on [being] ambitious and growing. And I'm still super ambitious, but also life goes really quickly. So it kind of goes back to this point that you made about knowing yourself or that we've been talking about, knowing what you want and why, and making sure you're doing it for yourself and not someone else. I was doing my first company for someone else, little did I know it. But this company is not for someone else other than our customers of course, but the internal drive, there's a clear foundation for that.

My own takeaway from Brett’s takeaway: whereas building a company is about getting to know your customer and creating a product they want, building your life is about getting to know your whole self and creating a life you want—companies and families and fitness routines and all. Big pivots are expected.

Full transcript below (or listen to the full episode here).

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