Bootstrapped startups and the shit I learn in therapy

For the second year, I used the Reflecting Forwards Notion template to do an in-depth personal year in review. Most of it I will again keep private, but for the sake of consistency (and having something to publish) here are a few excerpts and pictures.

2021 goals

My goals at the beginning of the year were to:

  • Do more active giving.
  • Move in with my girlfriend.
  • Spend time outside of screens... in nature and in books.
  • Build a second business.
  • Make Krit less stressful.
  • Spend time with my sister and friends.
  • Be active.

Theme for the year: Margin

Ohhhh buddy did I miss on the theme for this year. I wore myself thin at work, and the constant setbacks really ate away at me. I did not take any money out of the business. I did an okay job making time for myself and not working totally crazy hours, but I had a really hard time not thinking about work when it was stressful which was most of the year. I didn’t take on extra projects.

But on the plus side moving to Detroit has been great, even though it has been tough. I think I’m getting a lot better at communicating, although I still have a long way to go. I spent a lot of time with friends, and climbing has been really great. The automatic thoughts have gotten better, and I would say my mental health in general is better although work is a major drain.

Journal excerpts

  • Had a great day with Austin, talked about why doing this, even if we fail building unparalleled skills and network.
  • Thinking about woodworking, trying to create more and consume less, made a bench with Dad over the weekend.
  • Do I want to invest in your growth, or load the dice? It’s hard to load the dice but people are good at learning.
  • Buried Duck, buried him besides Indie, marked it with the stone from Iceland and put the bench Dad and I made beside him. Worried I wasn’t mindful enough, or went along with what others said instead of making the decision for myself. But the timing was right. I hope he understood how much I love him.
  • Po Boy ran away and I went to Detroit. Started a podcast with Sean and I’m loving that, haven’t felt super motivated at work otherwise.
  • Feeling happier than I have in a long time. Relationship, climbing gym, getting self-care dialed in. Worried about sales.
  • “To choose doubt as a philosophy for life is to choose immobility as a vehicle for transportation”
  • We lost a big client, Scott’s advice “have some arrogance,” don’t compete on speed and availability.
  • Spent a bunch of time reflecting on north star for the team, what am I uniquely good at, what do I most enjoy doing, what am I bad at, what do I dislike?

Looking back on my journal entries from the year I can see the ups and downs. One of the biggest lessons from this year was learning to view anger not as something to be ashamed of but as a warning sign that I need to adjust something in my life.


Core values: Courage, Love, Creativity, Honesty, Beauty

  • I think it was a pretty courageous year. It was scary to put Duck down, to move to Detroit, to keep going at work. I don’t think there is anything I didn’t do this year out of fear that I wanted to or should have. Climbing has given me a very real way to exercise my courage on a regular basis.
  • Love was definitely present this year. Friends, relationship. I think I could talk to my college friends more, talk to my family more, and continue to get better at how I communicate in my relationship.
  • The only bit of honesty I’m struggling with is Krit, is it the right thing for me to continue building Krit? And I think that’s more of a situation where I don’t know.
  • I’m not sure beauty is right, maybe this should be balance. It was not a super balanced year. It feels like even with all the time spent with friends, this year was a lot about struggling at work.


  • Turnover at Krit was really hard on me. I had to fire people for the first time this year, and we had a number of really talented people leave. It really ate away at me.
  • Dealing with the end of Duck's life.
  • Dealing with a client who refused to pay a significant amount of money, and with a slowdown in leads.


  • I’m proud of my move to Detroit, and how much effort I’ve put into finding friends, hosting people, and getting to know the city.
  • I moved in with Maddy, and have put a lot of energy into our relationship.
  • I started the podcast with Sean, and we have put out 13 episodes with 580 downloads.
  • I moved us into cybersecurity officially, and rebuilt our leadgen. It’s still a work in progress, but we’re in a much better place than we were this summer.
  • I raised our rates significantly, raised salaries, and improved benefits. We hired 3 great people.


  • I learned about the roles of an agency, and really started to think more about what it means to be a Principal through DCB.
  • We have begun the transition to an FTE/flat-fee pricing model
  • I learned to climb at a consistent V2 level, and climbed outside for the first time
  • I improved the way we set goals
  • I learned to recognize when I’m losing my temper frequently as a warning sign that something is wrong
  • I got a lot better about communicating my needs instead of reacting passive aggressively with Maddy
  • I learned that providing specific direction doesn’t limit people’s creativity. It gives them the bounds to discuss and challenge the way things are done.
  • I learned to identify which hat I need to be wearing for a given situation.


  • What will it take to make Krit a place where people want to stay?
  • Should we focus on making Krit a place where people want to stay?
  • How do I show up best in my relationship?
  • Do I want to continue being an entrepreneur?
  • Is security still the right field for us?

Moments of awe or wonder

  • Drummond - seeing the landscape, sailing with Wyatt, going back and forth from the sauna.
  • Lake Michigan - seeing the waves and the whole lake for the first time. Watching the sunset with our friends.
  • Food - Takoi, Supergeil, Mink, Momofuku.
  • Finding Po Boy.
  • Burying Duck.
  • Seeing the Texas hill country at golden hour.
  • Seeing Joe and Laura get married.
  • Looking out at the Red River Gorge from the top of that 5.9.

Goals, projects, and thoughts about 2022


  • $150k per year in salary
  • Learn to lead climb
  • Host a dinner party
  • Go to London
  • Refine marketing process
  • Hire and train an account manager


  • I want to be content with what I already have - my job, my girlfriend, my home, my life.
  • I want to reflect on where in the business I am at my best and my most fulfilled and find ways to lean into that.
  • I want to start a project with my sister.
  • I want to climb, and have adventures, and make time and space for things that aren’t for social media or for a blog or a business but are just for me and my community.
  • At the same time, I can’t shake the desire to start the newsletter back up and create a regular writing habit. No matter how many times I try and fail I keep finding myself daydreaming about writing.
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