Startup Diary
Monthly summaries about how it's going
2025: Just Ship
November: Shipped the Now view. Lots of marketing, yet #s still flat. Need to figure out distribution.
October: Shipped the Day view. Deprioritized sub-calendar support—was a huge time suck and not the bottleneck. SMH.
September: Finally shipped the recurrence feature! Helluva lotta work, proud of us.
August: Quit my comfy corporate job to go all-in on an open-source productivity app that generates $0 revenue...again. Let’s go!
July: Onboarded BE dev, making better progress now. Still ‘behind’ schedule. Need to ship more and add pricing.
June: Increasing volume: 2 longform YouTubes / week + Shorts. Hired backend developer.
May: 70hrs/week average, still going strong. Day 260 in a row. Finished readonly recurrence, added waitlist & gathered feedback. Cookin’
April: So locked in, coding for 3-5 hr every morning on week days, 4-6 on weekends. And weekly Youtube. But... still not done with recurrence feature, not even the read-only part. Gonna descope, fire myself, and hire a backend engineer. This is too slow.
March: Delayed launch from end of this month to end of next due to underestimated recurrence feature. Started getting up at 3:15am so I could have more extended focus on Compass before work.
February: Locked in. Just coding and working out.
January: Goal for 2025: Make Compass profitable. Started phase 1/4: Making it good enough to use.
2024: Stay Consistent
December: Hired a part-time open-source contributor for Compass.Green Bay is a good environment for focusing on my work. Gonna stay here.
November: Crashing at family’s place in Green Bay. Coding every morning still.
October: Locked in: coding Compass every morning, no distractions
September: Bad news: I don’t care enough about finance either. Good news: I’ve been coding for 20+hr / week on my own. Bad news: it’s been on Compass, the free app that no one uses yet. Good news: I’m at peace with that.
August: Worked from NYC for 2 weeks. Focusing on a new domain I’d genuinely enjoy: finance
July: Good news - the biz plan is valid. Bad news - I don’t care enough about it
June: Made plan for next startup
May: Went to NYC for Vercel conference. That’s the place for me.
April: Went to San Jose for AI conference. Need to move, either there or NYC.
March: Took last-minute trip to SF to attend a private indie event; so cool to hang out with my people.
February: First month with enough money that I could breathe
January: Theme for 2024: stay consistent. Specifically, posting to YouTube and up-leveling skills
2023: Create Magic
December: Finally got paid, thank god
November: Focused on keeping contract. So broke; feel like a cornered animal.
October: No buyers. Open-sourced it. Started contract with Costco as frontend dev.
September: Decided to try to sell Compass. Need $. Tired.
August: Decided B2C ain’t the move. Looked into B2B pivots. Found 3 total, 1 I really like.
July: Committed to pushing updates on 15th & 31st each month. This month was fixes and recurring events (part I).
June: 6 rounds of interviews for a SF startup. Got through all of them, but they decided to go a different direction. Sigh. Just want $$ so I can invest more in Compass.
May: Lots of meetings and job searching, but refused to let Compass stall. Consistently carved out a few hours at night to chip away at the next update: monthly (+ weekly) sidebar items. Will be much more usable afterwards.
April: Launched reorder feature. Reaction was ... meh. Decided to start looking for FT work after talking to a lot of bootstrappers at a conference.
March: Started the someday list reorder feature (tricky!). Got personal life back together, thank god. Coworking and friends help a lot.
February: Big backend feature that is important but no one will notice (handling Google’s 410 errors). Released a few minor updates to the app: shortcuts & migration. Launching hasn’t been the sustained energy booster that I hoped it would be. Feeling unmotivated & lonely. Planning to try coworking space next month
January: Started rolling out the MVP to the waitlist. Conflicted about promoting something I’m not super proud of, especially to friends & family. BUT, relieved to stop worrying about whether it’s ‘ready’ to launch and instead focus on how to make it profitable
2022
December: Got a second PT job. Automated sync maintenance. Fixed sync bugs. Sick of sync.
November: Lots of transition. Moved into new place, got new (old) car, got PT job. Haven’t opened IDE for 2 months now. Bummed about lack of progress, but know that giving myself time was the right decision.
October: Painful breakup. Tried to get my feet back under me re: emotions, $$, life direction. Didn’t have much energy left for work.
September: .... more sync fixes. (Shoulda never included sync in this version.) Startup Week Twin Cities conference rejuvenated my lonely soul.
August: Despite money dwindling, visited Italy with good friend. Feel refreshed, less anxious. Continued sync fixes (after finding last month’s fix inadequate).
July: Finished refactor, fixing auth and sync issues. Learning to become more accepting, less stressed when things don’t go as I initially planned.
June: Refactor was maddening. I’m close to paying off all the technical debt. Can’t wait to move on and work on features again.
May: Finished Someday List, but that exposed some show-stopping bugs. Have been putting off refactoring part of the code that has a lot of logic, but decided I need to clean it up for things to work now. Getting antsy. Sigh.
April: Got 3 people to try out the app. They like the feel, but it’s not enough to get them to get out that credit card. Almost finished with the Someday List feature. Gotta figure out a better hook/feature set.
March: Lots of skiing time with friends & family made this a slower month, but still fixed lots of issues. Turns out all-day events are event trickier than I first thought. Only one more task before I start testing it out with a few new users.
February: Tackled the most complex issues for the first version (I hope!): all-day events. Trust me, harder than it sounds.
January: Update frontend enough to get Compass working (in the most generous sense of word). It syncs between GCal and can update events. Secretly deployed to the internet and using it day-to-day while making updates. Gettin’ close!
2021
December: Wrist thankfully recovered enough to code again, backend nearly done. It’s been hard to code for so long without a release, but I’m seeing the light at end of tunnel.
November: Man, this month was rough. Needed wrist surgery after being bit by a cat; wasn’t able to code. Moved to Saint Paul, Minnesota to be closer to family and a tech hub.
October: Maniacal focus on development paid off. Calendar’s UX, architecture improved a ton so far. Frontend 50% done, backend 25%.
September: Launching was humbling. Big takeaway: Product’s gotta be easier to use, more aesthetic. Started working on improvements. This next version is gonna be sweet.
August: Finished the working prototype, which has these features: focus mode, priority tagging, analytics. Notified 130 waitlist subscribers. Now we test, get feedback, rinse, and repeat.
July: Code, code, code, code, code. Cut out all the non-essentials: Twitter, newsletters, fluids. Singularly focused on launching early
June: Pitched the app all over the internet and started coding the first version. Currently 70 people on the waitlist - exciting! 🤘 Goal is to focus on launching the first version next month.
May: Refined idea into a reimagined calendar app. Launched the landing page and finished the prototype. Feedback has been positive! This is by far the furthest I’ve gotten on anything and is the most viable. Now focused on growing audience and getting initial product out there. Hired a part-time dev to help out.
April: Yes, virtual co-working is a thing. And. My product ideas could be better applied in a different context, namely: building a better system to structure our time. I don’t see a comprehensive way to do this; how we organize our time is scattered among calendars, to-do lists, notebooks, and kept in our heads. Despite how frustrating it is to keep pivoting, I think it’s the right move.
Creating wireframes in prep for a demo/pitch event next week. Hoping to get some feedback that I can use to eventually (finally!) transition into developing the thing.
Feedback from event and other meetings has been positive! Started with conceptual images and have been converting them into an interactive prototype. Holding off on coding has been a good call so far.
March: Serious doubts about virtual co-working viability after testing an existing app with a few friends the past week. {Sigh} On second (forty-ith?) thought, there’s definitely something there with virtual co-working, just not in the way I initially understood it. {Pfew}
Interviewed EFF‘s Director on the podcast, which was a dream come true 🥳
February: Got feedback for idea of visualizing presence and making casual convos easier for Microsoft Teams. It’s possible and could be useful, but there’s some serious holes in the business & adoption model that I haven’t found a solution for.
Excited about idea of virtual co-working. Imagined possibilities and started thinking about the core value-prop and features.
January
Left my full-time gig and moved to Bozeman, MT. Feels good to be all-in. Now I just got to figure out how to make money. Put our Instagram and Facebook profiles to sleep. Those platforms suck.
2020
November: Scrapped back country map after deeming Gaia GPS good enough. Got feedback from people about their experiences working from home and using social media. Looking for potential opportunities.
October: Testing viability for a back country map app.
September: Created a podcast logo. Too busy with my boring full-time job.
August: Finalized & shared a client project involving contact syncing.
July: Focusing on the niche of geospatial web apps. Three reasons why: 1) geo data and apps are badass, 2) I already have experience building full-stack, scalable apps, 3) geo applications are on the rise thanks to an increase in data and computing power.
June: Scrapped the audio-reminder hardware idea; couldn’t see the potential for a market.
May: Switchback LLC is official! It just 30 minutes took and $50. Tickles me how typically-bureaucratic orgs have a knack for making things very smooth when it involves accepting money.
Testing out viability of audio-reminder hardware to make high-risk activities like rappelling less dangerous.
Made some silly videos sharing my ideas. Trying to put myself out there, not take things too serious at this point.