Bootstrapped startups and the shit I learn in therapy

For the first 19 years of my life I knew I was lazy.

I was smart, but I constantly slacked off. I found the smallest amount of work I could get away with doing and did no more.

I was often reminded that I wasn't living up to my potential. "If B's were all you were capable of that would be fine, but you're so smart. You could easily get an A," was a regular refrain in my house.

Everyone around me seemed to find it easy to get work done. Why wasn't I that way? What the fuck was wrong with me? Why was I so weak that I couldn't stand to do anything remotely hard?

It filled me with shame.

I'm a nerd, always have been. I wasn't fast or strong, my face was covered in zits and I got super nervous around girls. I was happiest with my nose in the book or hanging out with my Boy Scout troop. School was the only thing I was good at. And I kept fucking up at that.

It got worse in college. First, smart phones became a part of the classroom. Then I discovered I could get away with skipping most of my classes all together.

My grades started slipping, and I went from skating by, to struggling to keep up. The B's turned into C's and D's. Now piled on top of the shame, I started doubting my abilities for the first time.

The year I turned 20 there were two big changes:

1) I got diagnosed with ADHD

As my grades started slipping the shame piled up. I had to admit something wasn't working. I was beating myself up, and my grades weren't getting better. I take pride in being self-reliant, asking for help made me feel weak.

Note: this was a dumb way of looking at life. It's never bad to ask for help.

But the direction I was heading scared me. So I went to see a psychologist. Within 4 sessions I got a diagnosis. I had Attention Deficit Hyperactivity Disorder.

Puzzle pieces started to fall into place. When you have ADHD it feels like your head is constantly buzzing.

Tasks as innocuous as putting away clothes can be a trap. The extra time it takes to do something as simple as open the drawer is time for your brain to get distracted. And then it could be an hour before you remember what you were doing.

Note: If you're struggling with ADHD, check out the book Organizing Solutions for People With ADHD. It gave me useful tips, but more importantly taught me about how ADHD works.

2) I started a company

The spring of 2014 I started my company, Krit.

As the date of our first launch approached I barely slept. Around 4 am I would call an Uber, then my dad would drop me off on his way to work at 8. Some nights I didn't even leave the office.

Healthy? No. But I was working harder than I ever had before.

It's one of the greatest gifts I've ever received. Because one day it hit me. I was working harder than I ever had before.

I wasn't lazy.

I could work!

I actually got immense pride from working. It just took the right combination of motivation and constraints.

That spring was almost 5 years ago. Krit should make over $600,000 in revenue this year, and is now a team of 8. We've helped clients launch 8 new startups and 2 non-profit initiatives. We've built a small audience and products of our own. Our clients have sold their software to names like Facebook, Red Bull and Yale.

Getting diagnosed and starting the company showed me that I wasn't lazy. Now I had hope.

The pressure of ADHD as a founder

Unfortunately, hope is only the first ingredient. Learning I'm not lazy was powerful, but 5 years later I'm still fighting to make myself believe it. Those feelings didn't magically go away forever. They still come back in waves until I fight them back again.

Now, when they come back, the pressure is even higher. If I have a bad day I worry I'm setting a bad example for my employees or letting down a client. Getting behind can have major consequences. I often work extra hours to make up for the time I spent distracted and then feel myself burning out.

ADHD seems like an innocuous disorder. Everyone procrastinates right? So what, you can't stop bouncing your leg at the restaurant? So what you get distracted every time you see something shiny?

What makes ADHD dangerous is the stress and shame that come with it. The shame of feeling lazy, or dumb or socially awkward. The stress of not doing enough.

I'll be halfway through a team meeting and realize I haven't heard anything that was said. That's ADHD.

I'll take a break to read an article and hours will go by before I realize what's happened. Not minutes, hours. That's ADHD.

ADHD can feel almost like time-traveling.

It doesn't have to be something unproductive like Twitter that initiates it either. I'll be working on a task, when I'll remember something else that needs to get done. I'll start working on that, and hours later realize the first task is still half-completed.

As I'm writing this I've stopped half a dozen times to wipe dog hair from my computer. Pulling my mind back to the article feels like reigning in an unruly horse.

How I deal with ADHD as a founder

Over time though, I am getting better at managing myself. Here are ways I've found of coping:

Prioritize obsessively

Start every day/week with a task list.

When you're fighting ADHD, external stimuli are your enemies. Unstructured time (when your mind is wandering) is exactly when those stimuli attack.

I use Todoist these days to keep my list up to date. In the past I've used a straight up note or even a Slack message to myself. The key for me is for it to be super fast to add and reorganize tasks. The structure also has to be super simple. Too much organization is bad for someone with ADHD, because it's a chance to get distracted.

Todoist has a great mobile app, and makes it super easy to prioritize tasks and move them between days.

Make sure to keep your daily list small (I try to cap it at 5-6 tasks) and don't beat yourself up for moving things around. That unstructured time where you get distracted can also generate creative ideas.

Start with a small win

I often start with a lower priority task that I can get knocked out quickly. I've heard lots of people advise you to start your day with the biggest hardest task. For me that's often a recipe for disaster. A big, hard task is a chance to get distracted. Then I feel worse about myself, and I spiral.

Starting my day with a small win is a good way to remind myself that being productive feels good. Sometimes I'll also knock out a low priority task first just because it seems fun. Because fuck it, I'm my own boss, and it's okay to enjoy that.

Embrace minimalism

Reducing the visual clutter in my world is a must. My brain constantly feels busy and out of control. Visual order in my surroundings help to soothe that feeling of chaos.

Minimalism also serves a practical purpose for people with ADHD. Every thing that occupies my plane of view is a chance to get distracted.

I've been meaning to finish this book, I'll skim through and try to find my place... Oh I forgot about these grip trainers, I really ought to get back into rock climbing... Charger! Dammit Andrew you came over here to charge your phone!! That was the whole point... god I need to do my dishes, but first let me sweep...

The same goes for digital minimalism. Notifications are a rabbit hole. Fun looking icons are a rabbit hole. Everything is a potential rabbit hole.

I've been working on making my phone dumb again. First, I removed all of the social apps. Then I turned off notifications for everything except a few apps I use to communicate with my friends. I even turned off the notification bubbles on my email app.

My phone

Raise money

I'm a big fan of bootstrapping. I love the conversations the bootstrapped community has around health and entrepreneurship. This group of people is bucking the idea that you have to build something massive and work yourself to the bone in order to be successful.

But raising money has one underrated advantage. It lights one hell of a fire under your ass.

Raising money has one underrated advantage... it lights one hell of a fire under your ass.

I consider myself a bootstrapper.

That's only partially true. When we started the company, my co-founders and I had been trying to get something off the ground for several months. Then we got accepted into an accelerator program. They put $16,000 into our company.

The email where I found out we were getting $16,000 to start Krit. 

While it wasn't much, without that money our company wouldn't exist today. It held us accountable. It gave us the pressure we needed to get started. That's a powerful feature.

Hire a coach (or editor)

Raising money won't always be an option, so you'll have to find other ways to hold yourself accountable. Start by figuring out what excites and motivates you.

For me it's people and relationships. The surest way for me to get something done, is to know that I will be letting someone down if I don't.

The capital we raised was the first example. But a more accessible option is to hire a coach. Or, if you're a writer, hire an editor. Regular meetings with another person are a fantastic forcing function. I may get the work I promised them done the day before our meeting, but I'm going to get it done.

Do work you enjoy

Everyone should be lucky enough to find work they enjoy. But for those with ADHD it's a requirement if you want to be successful.

I started my career as a programmer. I enjoyed the problem-solving aspect of it, but I hated cranking out code day after day.

As a result, I wasn't very productive as a programmer. I regularly missed deadlines, and the quality of my code was average at best.

The biggest boost for my productivity was stepping away from writing code full-time. Two years ago I transitioned from coding to a more traditional CEO role. I handle sales, marketing and whatever needs doing on a daily basis. I'm much happier than I was when I was programming.

I was privileged enough to be in a position where, at 23, I was running my own company. Because of that position I was able to change my role without getting a new job, or anyone's permission. For that I am incredibly lucky (and thankful).

If you're not in that position, it will be harder to experiment and find the work you love. But if you have ADHD, you have to try. Like every other tip here, it's about reducing the chances of getting distracted. When you enjoy the work, it becomes easier to get started, and you're less likely to look for distractions.

Listening to this podcast about chasing your motivation was super affirming for me.

Finding working you enjoy isn't a magic cure-all. I still have to do things I don't want to do. I still have to constantly work on my self-discipline. But it is leaps and bounds better now than it was just a couple of years ago.

The advantages of ADHD

The disorder also has advantages. The biggest advantage of ADHD is the ability it gives me to think creatively.

That sounds vague, so let me try to explain. I'm horrible at completing simple, repetitive tasks. I'm terrible at time management, and conceptualizing time in general.

But the types of tasks that the world puts into the bucket of "creative" I tend to be quite good at.

✅ Thinking up names for new products

✅ Creating a high level strategy

✅ Figuring out the perfect wording for a company goal

✅ Writing (when I can get started)

✅ Persuasive conversations (aka sales)

✅ Solving poorly-defined or murky problems

These are all things I can do.

While I have no proof that ADHD is the cause, there have been studies that indicate it is connected to creative thinking. And from my own anecdotal evidence it holds up.

A note on medication: When I take medication I feel these skills being dulled. I can't think as quickly, I'm not as outgoing. ADHD medication also contributes to an increase in anxiety, and so for me it's not worth it. If you're struggling you should absolutely try it. For some people, medication is a must. Don't ever feel bad about taking it if it helps you.


I don't ever want to use ADHD as an excuse or a crutch. But if I don't acknowledge the challenges the disorder creates I can't develop coping mechanisms. So I'm acknowledging those challenges and I'm sharing them here. My hope is that others facing the same challenges know they're not alone.

If I don't acknowledge the challenges the disorder creates I can't develop coping mechanisms.

Here's what works for me:

  • Fight shame. It's an asshole of an emotion. Don't let it rule your life. You're not a bad person just because you have done bad things.
  • Find a way to create healthy pressure. Raise money or hire a coach. Whatever it is, invest time learning what motivates you.
  • Prioritize obsessively. Lists, lists, lists. Don't overcomplicate it to start, a blank sheet of paper works great.
  • Start small. Look for a small win to start your day off and build momentum from there.
  • Embrace minimalism in your digital and physical life. The fewer visual triggers to distract you the better.
  • Find the work you love. The internet has created a new world where any niche can turn into a sustainable profession. Worry about the finances later, focus on finding work you enjoy.

And remember, like everything in life ADHD is a two-sided coin. The disorder that drives you crazy is likely responsible for some of the best parts of you.

Chin up, you got this.

Final note: It took me 4 months of leaving this piece half finished and coming back to it in order to finish it.

The awesome illustrations in this blog post are all courtesy of Dani Donovan. Follow her on Twitter or subscribe to her patreon to help support her awesome work.

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