Fall in Love with a Problem, Not a Solution

What I Learned | Season 4, Episode 7

Feb 23, 2022

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Hey y’all!

Today’s post is a risky one. My hope is that a few of you enjoy it, and the rest of you don’t cancel me or judge me too hard. :)

Here’s the premise:

I’m always “working.” It looks like work to others, but it feels like play to me. And that’s how I know no one can compete with me on it. Because I’m just playing, for sixteen hours a day. If others want to compete with me, they’re going to work, and they’re going to lose because they’re not going to do it for sixteen hours a day, seven days a week.
-Naval Ravikant

This is not a post about how to achieve work-life balance. If you’re allergic to #hustleporn, you may have a strong allergic reaction to today’s post — in the least, you may pick up a slight rash.

Please don’t cancel me.

Let’s get into it.

Context: my 10-year journey

It’s worth reminding new readers of who I am, as this context will be super helpful for today’s post. Feel free to skip this section if you don’t care (I won’t be offended).

After college, I stumbled into a job at a software company. It was an entry-level sales job in Charleston, South Carolina. I was selling loan origination software to banks and credit unions. I did not like the job, but it taught me a lot.

I eventually quit, and found my way in the door at a startup, as the first employee — I moved to San Francisco for this job. I worked there for four years, starting in entry-level sales, then quickly up the chain, and eventually managing the entire sales function. These four years were my “MBA.” Unfortunately, at around $10M ARR, the company plateaued, did a round of lay-offs, then another round of lay-offs, and I saw myself to the door (they were relieved to lose an expensive manager).

From there, I decided to acquire (technically: I just bought the assets of) a piece of software that our sales team had used and loved. 18 months later, I realized this wasn’t going to be a home run, and my co-founders and I decided to take an early acquisition offer — it was a solid “base hit.”

Last chapter before today. After leaving the acquiring company (it is hard to hand over the keys to a car you built) I had an existential crisis; I was trying to figure out: Should I Start a Startup? I consulted a bit during this time of explorationfor, then the pandemic hit, and was lucky to have Zoom as a client, so they made me a job offer, and I could sit comfortably in the chaos of Zoom, while I continued to have lots of conversations with mentors, friends, and family about what I should do next. I eventually decided I wanted to make the irrational decision to take another crack at a startup. I knew in my bones I had to Go All-In.

So, that’s the ten-year journey that got me to where I am today: starting Groundswell, which I plan to work on for (at least) the next ten years.

Choose your own adventure

Now that you have the context, know that this post is not for everyone.

In fact, I would go as far as to say, this isn’t the ideal life most people should live.

But for me, I’ve learned that I honestly love the work that I’ve found. I love building software companies, and figuring out how to scale them — the technology, the people, the processes, the systems, and all the problems that come with early-stage software companies.

In a venture-backed world, the competition is fierce, especially on the cutting-edge of a new trend. If you bootstrap a company, you likely will get your lunch eaten by a competitor who has a war chest of cash to deploy on engineers, sellers, and marketing budget. I knew this going into Groundswell, but with this knowledge comes the reality that I have to work a lot of hours, for many years, to succeed.

I’m always “working.” It looks like work to others, but it feels like play to me. And that’s how I know no one can compete with me on it.

Choose a problem wisely

This leads me to the point of today’s post.

When I was selling to bankers, I was bored out of my mind. I couldn’t relate to them, and I didn’t care about the problems they were trying to solve… that the software I was selling could help solve. It is critical to find a group of people that you love working with and solving problems for, and you’ll be energized every day to work with those specific people to help solve those problems together.

When I was at my second startup, we sold to online retailers. I had personally sold some stuff on Amazon, eBay and Craiglist in college, so I was very curious about the strategy of online retailers. It was fun to talk to these people all day, every day. It was exciting to read articles about the macro-trends in the space. I was constantly learning, but again, it didn’t feel like work.

The problem I am solving at Groundswell is big enough that I can work on it for 10-20 years. But it’s also interesting enough to me, that I can be happy spending 10-20 years on it. It’s important to have both. Big problem + personal interest. And the people I talk to every day are trying to solve problems that I’ve become obsessed with.

I don’t think you need to (or even, should) fall in love with a solution (or product). Especially at a super early-stage startup, the product will likely morph and evolve over time. But the problem you are solving for, and the type of persona you’re solving for, they likely will remain the same.

That’s why you should fall in love with a problem, not a solution.

At Groundswell, we are helping GTM teams solve three fundamental problems:

WHO should you reach out to next? (Company and/or person)
HOW should you reach out? (Sales rep? Automated email from marketing? In-app message?)
WHAT message should you send? (Automatically personalized based on context of #1)

This week, a friend texted me how things were going with the new company. I replied something along the lines of “I am having so much fun. I would do this if I wasn’t getting paid.” And I meant it.

I have fallen in love with the problem we are solving.

Setting intentions

Working a lot requires sacrifice. And I have chosen to not put work first in my life, even if I do give it a lot of my time.

My “intentions” for this year are simple:

Personal = “Present”
Health & Wellness = “Patient”
Work = “Obsess”

I don’t want to miss out on family time, that is always first.

I don’t want to compromise my health: physical, mental, and spiritual — these are the foundation of everything else.

But, when it comes to my work-life, I am going to obsess in this season. And in a venture-capital start-up, I think it’s a non-negotiable.

Marc Andreessen @pmarca

@Austen Most of the great founders I've known work 80+ hour weeks, especially in the first decade.

Singular focus

As I write this post, I keep having self-doubt pop up. I keep worrying about what people will think about this — I don’t care if people who unsubscribe, but I do care about friends, family and colleagues who may look down on me for these thoughts.

But I want to put my stake in the ground. I want to call my shot. Because like I said, it feels like the first decade of my career, with all its ups and downs, was all just to set me up for this second decade of my career, of which I’ll be working on one single thing: Groundswell. This is both terrifying and relieving. Putting all my eggs in one basket scares me, especially as someone who is risk-averse (I am), it’s an intense feeling every single day. I see opportunities come across my desk often. But I’ve chosen to stop even glancing at them. The upside to a season of singular focus is that I’m able to work each day without any distractions. I’ve changed out crypto and NFT podcasts with B2B SaaS podcasts. I’ve unfollowed certain accounts on Twitter, and actively looked for revenue leaders to follow there instead. I’m architecting my life, in this season, to be obsessed.

Competition

There are several founders building competitors to Groundswell that have 10x the funding we do (or even 50x). Why am I not scared that they’ll outwork me and win in this market?

If others want to compete with me, they’re going to work, and they’re going to lose because they’re not going to do it for sixteen hours a day, seven days a week.

Fall in love with the problem you’re solving, so that you can obsess over it, and you won’t work a day in your life.

Obsess and perfect your craft. Be maniacal precision, even if no one is looking.

See you on the field.