Bootstrapped startups and the shit I learn in therapy

For the first month of my freshman year of college, I talked to everybody and tried everything.

If we were standing next to each other in line at the dining hall, you’d likely hear, “Hey I’m Andrew. Where are you from? How’s class going so far?” If there was a club, meeting, or activity of any kind: sign me up.

The result was I found a group of incredible friends, a club where I would pour in hundreds of hours over the next 4 years (shout out to the Daily Gamecock, top 10 student newspaper in the country), and a major that eventually led me to start Krit.

Four of my closest friends, all of whom I met freshman year.

I tend to apply this brute-force strategy to many aspects of my life. For those not in cybersecurity, in a brute-force attack, the attacker attempts to gain access to a system by literally trying every single username and password combination. I use almost the same approach in my life.

I start by throwing myself at the problem and trying a little bit of everything, often all at once. At this stage, I’m not being efficient at all. I’m bouncing around in a way that can feel chaotic. The point is to move quickly and maximize exposure to different ideas.

When rock climbing, I often use this approach to find new projects. I’ll walk into the gym and try a lot of boulder problems once or twice. Then once something piques my interest, I’ll spend the rest of the session working on that.

Someone much better at bouldering than me.

I start with a lot of options, then follow the signals and refine my focus. The signals might be a gut feeling about what I’m enjoying the most, or—if we’re talking about work—it might be the market responding with actual dollars.

The hardest part is having the courage to listen, follow, and say no when you start getting these signals.

When we were starting Krit, we used this approach to find the right positioning. For our first couple of years as an agency, we would do anything for anybody: single-page websites for local nonprofits, custom job board software for a Cannabis startup, highly polished portals for insurance providers. These are all real projects we took on in our first couple of years in business.

Over time, we found there was a market for product development, and so we refined our focus. But we still worked across a wide range of industries, from legal tech to fintech, healthcare to grocery deliveries. That is, until we started getting more and more work in the cybersecurity space, and eventually followed those signals.

Today, cybersecurity products are our primary focus.

I’m using this strategy now to figure out how to revamp our marketing efforts in this new space. Over the past 3 months, I’ve dabbled in influencer marketing, podcasting, cold email, organic social, business development, and speaking. We’re seeing early signals that business development is going to be a strong channel, and influencer marketing may help seed our organic social efforts.

Why does this approach work?

It overcomes our weaknesses

As humans, we’re bad at predictions. We don’t know how market demands are going to shift over time, or what other people are really going to do with a product or piece of content.

We’re also bad at understanding ourselves. As weird as that is to admit, our brains are a complicated mess of biases and emotions. We all have stories we tell ourselves that might prevent us from talking to someone or trying something.

Brute-forcing a marketing strategy, R&D initiative, or even finding a new hobby means accepting you don’t have the answers and you’re prepared to put the appropriate amount of work into solving the problem.

It keeps you from getting stuck

It’s so easy to get stuck in decision-making mode that there’s a fancy term for it, Analysis Paralysis. The reality is you won’t ever be successful at cracking that tricky problem if you don’t try. By admitting you don’t have all the answers and accepting that most of your experiments probably won’t work, you’re lowering the bar and making it easier to get moving.

It buys you more luck

There is an element of timing that impacts nearly everything we do. Our personal tastes change over time, and market dynamics are constantly shifting. The more experiments/potential-solutions/hair-brained-ideas you try, the more lottery tickets you’re buying and the more chances you have to win some sort of prize.

Permission to apply brute force

I’ve tried multiple times to put some structure behind a brute-force strategy in different aspects of life. In marketing for example, there’s the Bullseye Framework popularized by the book Traction.

There’s a great blog post on Bullseye from Baremetrics

But whether it’s a symptom of my ADHD, a deeper personality flaw, or just the reality of creative work, I often find the most success when I embrace the messy uncertainty and just start trying things and going with what feels right.

Are you stuck on a difficult problem and struggling to find the right strategy?

Consider this permission to brute-force it.

You’ve successfully subscribed to Andrew Askins
Welcome back! You’ve successfully signed in.
Great! You’ve successfully signed up.
Your link has expired
Success! Check your email for magic link to sign-in.