What’s poppin

If you notice my Linkedin, you’ll notice Keepsake shut down in mid-feb. I didn’t make that decision until 2 months after, when I realized I had not worked on it in 2 months. It did not spark joy, so I made the decision to end it. It was a ride, 1200 hours (tracked) spent over 7 months.

Through Keepsake I got my first real b2b user, a kind lawyer in Massachusetts. He was our first beta user, and the only one to ever try it clients, the first one being dec 15. He used it with 5 clients afaik. 1 of them on jan 2 lost 2 hours of their time filling out forms, because they didn’t click the save button before closing the page, despite the save warning. The next week, autosaving was implemented to prevent that.

I learned how to find competent offshore developers for dirt cheap, $500-$700/mo, and interview them. Made a few mistakes in my interview bar, but I’ve raised it 2 different times. I also realized how few people wanted to do startups. I tried recruiting 21 different competent developers online. A quarter had full-time jobs and didn’t want to do anything else. A quarter wanted money. A quarter weren’t in the mood for a startup. Finding someone like me, at the right time in their lives, with the right mindset, with the right (dev) skills, is almost impossible. So I had to resort to hiring people, mercenaries, which I’m not a fan of. But I needed help. Hired 4 technically. Fired 3. The last one did great and he is still with me, but as a friend now instead of an employee. He was a 4th year student in philipines who just graduated.

I also learned a crap ton about sales. I’m a decent salesperson now. I can cold email, cold call, use Linkedin/other tools to find leads and get their phone/number. I did a business minor and none of this was taught. For $300, I learned 100x more than my business minor which cost me $10k.

Since then, it’s been 4 months (mid-feb to mid-june). I will divide up this time into 3 parts: 1mo, 1mo, then 2mo. I will start with the last 2mo, as it’s where I have been doing my own thing.

Mid-apr to mid-june

I won’t lie, the first month was a blur and a very unproductive time compared to the past 2 years. I was sleeping at 6am for most of it. My sleep schedule degenerates when I don’t have something I’m excited or focused about. I’m living off of vibes, doing what interests me. I was very uneasy about it at first, as it means I’m not planning my days hour by hour like I used to. I’m not making consistent progress daily.

But I’ve become comfortable on living day to day and more freely. I’m doing what interests me and I’m happy. At the beginning, there’s been days where I haven’t done anything productive, just reading korean comics or anime recaps on yt (saves time compared to the whole thing). That’s not me anymore though, I’ve had my fill and the fire is lighting up again.

I did do a couple hours of job searching throughout, but the job search grind soulless and boring. It does not spark joy. I already did plenty, starting from even before graduating, and from 1200 applications I only got 4 technical interviews. A couple more recruiter screens that didn’t work out. For example, in the first week of june, I got 2 recruiter screens. One YC startups I applied to, and one for neuralink (surprisingly). Generic rejection emails a couple weeks after the screenings. 0 real feedback on why. Lazy recruiters/hiring managers. They don’t even explain their ideal candidate. There is no feedback from this system that helps you improve.

So I am not job searching anymore. I am going to do what I enjoy: startups.

I will give myself the next 3 months, until the end of august, to find a startup idea to pursue. My goal is to find an idea I can get $100k ARR worth of LOIs signed before I start building. I’m much better equipped now at finding a good idea, because I’m decent at sales after cold calling lawyers for 150 hours at Keepsake, and learning about all the sales tools out there. I have a ton of startup ideas. Now it’s just a matter of validating them.

I recruited 2 of my friends who were with from Keepsake to help out in my validation efforts. Them 2 and I were the team right as we shut down. They’re reliable and solid programmers. Together, we make a killer dev team. We’ve been brainstorming ideas here and there since shutting down, and they are free full-time like me. One is in Illinois, the other in Philipines.

My plan is that each of us will own an idea and validate it through the proper outbound channel.

I’m exploring the GIS space (geography and mapping tech) since mid may. I’m solely using Linkedin for outbound and it’s been great, amazing actually compared to cold calling and emailing (with lawyers). Best response rate I ever got at 10-15% of connection requests netting a response.

I’ve sent 300 connection requests so far on Linkedin, getting 20 answers to a list of 7 questions I send. These range from people with different job titles, from GIS analyst to GIS director.

I also netted 2 calls with 2 directors, one being 30min, the other an hour.

The first call was in mid may with a GIS director of a consulting firm with 11-50 employees. He had 15 people under him. Friendly and open guy, it was a 1h long call, but not too valuable in hearing any pain points. He did give me some tips on how to use workplace politics to your advantage. This guy was a master at that.

The second call was 4 days ago, I had a 35min call with the public works & water utilities director of a city of 20k: Evans, CO. Talked to him while he was driving to work conveniently. One of the most interesting conversations in my life. He had a pain point regarding the software they used to send out field teams to repair water pipes.

They were a lower income city, so their budget was limited, and they used Brightly. But they had issues and if I remember right, they stopped using it. When I asked him what software his department uses to run their field operations, he started with “this is a sore point”. The first thing he remembered was pain. He said he wished there was an asset management software that integrated better with their ticketing system.

Another quote: ”… how we build that information in is a huge challenge. Our goal would be to have something a little more built out, and a little more field friendly. When our water team is out there, they could have a tablet and GPS beacon. Vs. Some cities have a whole team that trails these teams and updates their systems”.

“If we can find a company that does an all-in-one solution, we’re not the only utility using off the shelf platform for utility billing and customer service. We haven’t been able to find one of those off the shelf tools, without a little bit of customization”.

“We had a half-baked solution to begin with, and with the 3rd system, we’re forced to be creative, changing that platform yet again”.

He said the current solutions out there price based on population, but a low income population like his will bring in less money than a high income one. Keep in mind that he manages a budget of $19m. A lower budget for a city of this size probably means instead of being to afford a solution that costs $100k/year, they can only afford $50k/year. This is big bucks in general.

At the end I said I’m into startups and if enough people have the same problem, I might build the solution. He said “I would greatly appreciate that, especially if it’s budget friendly, which is what we struggle with. All the smaller companies are getting bought out by the bigger one and jacking up the prices.”

I called him using google voice (easier to talk on vs my phone), and recorded it. Glad I recorded it because there was so much value in that call. I will review it later to help guide my future questions to other directors. I learned about problems I never knew existed.

I found him by luck. I was looking for power utility company directors earlier the day earlier. Somehow he came across and I sent him a connect req, not knowing he worked for a city. And now I learned about a whole new class of customers: city utility departments.

This call gave me the idea that I should talk to other directors like him, as they may have similar problems. I opened up Linkedin search and typed “public works director”, and I got page after page of results. Neat.

The next day (Friday), I sent 20 of connection requests and of those, 3 replied within 72h saying they are happy to answer my questions. I booked a call with one for Wed 10am, he is the director of Glendale, CA. Huge city with a middle class population at 180k. I am betting that the budget will be higher and challenges much different than the first guy I talked to.

If I can talk to 50-100 of such directors, I think I can find out where the gap in the market here. I see the spark of opportunity. And it’s fun talking to different people, learning new things, and formulating my questions. Problem discovery is fun. A billion times more fun than job searching…

The first startup

Let’s backtrack now back to mid-feb, when I jumped ship from Keepsake to another idea, inviting my 2 Keepsake friends along. I joined a pre-revenue startup in the home contractor space. It’s very software heavy because a HVAC company might have 10 technicians and will pull in mad cash. And they need a lot of paperwork and coordination to run smoothly. ServiceTitan is the market leader, charging $269/technician/mo, and their feature set is HUGE. Invoicing, dispatching, contract management, customer communication, etc. The idea was to go head to head against them and the other players in the space.

The founder was director of operations for his dad’s company in new york for 4 years, and wanted to build a better solution. Hard working and responsive guy. But long story short, he was building before validating. He had his father’s company, who wasn’t the ICP according to him, lined up for the pilot. The pilot started a few days after I left, and it went poorly due to bugs.

Why was the pilot being done on a non-ICP customer? His dad wasn’t excited for it, as they were using some 20 year old software that looked ugly but did the job.

He had a discord community of 20 business owners in the space, but didn’t call with every single one of them to see if they would switch to a totally new platform. Just text chats here and there.

Long story short, I told him to start cold emailing and calling, and he did a bit, but didn’t put in that much time. Most of his time was managing the linear. So I left. The MVP was 75%ish done, he had relied on a brazillian guy, Jason, who had a dev agency and brought in 2 devs of his own. Jason was a very interesting fella, he was 22 and was a lightning bolt programmer. I could write a whole article about him. He could write complex code quick. He was getting $2500/mo for him and his team.

Right as I joined, I also brought in 4 devs I knew to help out, who were crucial and did good work. 2 were new grads, 2 were students. All part time, all competent. The new grads were working full-time jobs, and agreed to help out after work. 2 in US, 1 in india, 1 in philipines.

3 were from Keepsake, and 1 was someone who was gonna join Keepsake back in dec, but it didn’t pan out because I found someone and he got busy.

When I decide to leave, I also messaged them and pulled them out when I realized this idea has no solid market potential. ServiceTitan raised $1.1 billion and their product is massive. Every part of their system is a codebase in itself. A bootstrapped company can’t compete with that. And they’re not even that expensive to start off with, I found out the price on reddit, which was much lower than how much the founder made me to believe. $269/technician/mo, when I thought it was $1000 or so.

Nonetheless, there is tons of mony in the home contractor space. probook.ai grew from 0 to $2m ARR in just 6 months (founder’s linkedin post). They do automated dispatching, and integrate with ServiceTitan. It’s a space I might return to in the future.

The second startup

Now fast forward to mid march. I see a nontechnical founder on reddit posting that they are not happy with their current technical cofounder, and that communicating with him is like pulling teeth. And a feature hasn’t been shipped in 6 months. So I messaged him saying that his cofounder is probably on the verge of leaving, because at Keepsake, when teammates put in significantly less hours suddenly, they left within 1-2 weeks later. Sample size of 3.

That wasn’t the case for the guy I talked to though, seems like his cofounder was coasting at 10h/week for a year or 2. The startup was making 85k arr, going on for 5.5 years, and breaking even. The idea was a documentation request platform for HR departments. This way, if a new employee is hired and HR needs 5 forms from them, this app can be used to send them the forms, allow them to sign it, and HR can know which ones they submitted and approve it, or resend if rejected.

I left ultimately because it was a red ocean, just like the first startup above. Competitors had richer feature sets, while being cheaper ($3000 vs. $5500 according to one comparison). One common argument the founder told me was that they would often lose potential customers, because they didn’t support the features they needed, such as role based access control. Well that $3000 competitor has all those features, while being cheaper.

When I joined I did’t read too much into the competitors. Wish I did. I though sales could compensate, and the founder showed me the sales kanban board, and it looked pretty full. But the month I was there, he hadn’t managed to get 1 sale. He did have meeting(s) with 2 leads, one school HR person, and another real estate lending firm. But no deal came out of it the time I was there.

He also had poor sales data and no real sales strategy. He didn’t record all his meetings. Any founder who doesn’t record their meetings is making a rookie mistake. You will not remember several important details during an hour call. I’ve had this happen to me at Keepsake before, I would rewatch the meeting, and then remember important details I forgot.

After every 50 or so sales calls, you should review all your sales recordings/feedback, and then update your sales strategy. This can range from the questions you ask throughout the demo to learn about your customer, to the sequence of features you use. Always make sure your documentation is not missing anything.

And when I challenged him once on why a feature was necessary, he said “I don’t need to convince you on why we are building features”. In these moments I found out he was an impatient, uncollaborative guy.

He should have shut down the startup when he wasn’t making a profit a year later. Good startups grow fast, $0-$2m ARR in 6mo for example. Just yesterday I talked to one YC founder, and they grew from $50k-$600k ARR in 5 weeks back in jan. All hugely profitable. The 2 examples I gave so far are in the top 10% of startups ofc, but generally they make healthy profit within the first year. Good startups don’t stay unprofitable for 5.5 years.