On 2 Years of Bootstrapping

2026.07.26

CLXII

[Happy Birthday; Fleeing Como; 4 Months of no Revenue; The First Customers; The Danger of Listening; Creeping to $100K; Getting Opinionated; Consulting Ceiling; A Product that Sells Itself; My Way]

Thesis: Starting a company is hard & non linear. I still don’t know what I’m doing, but you might find something from my journey useful.

[Happy Birthday]

My startup, WhiteWhale, turned 2 years old last week.

In that time, we've gone from no product, no brand, no customers, and a $3,000 investment from ourselves into a profitable, bootstrapped business that pays the bills & supports over 700 users.

Admittedly, just about everything has taken longer than either myself or my cofounder, Jack, thought it would. Likewise, we're still far from the ultimate, private destination we have for ourselves and the business.

But, we've come a long way, and for almost a year, have had a business that could support us.

This is a good moment to retell parts of the story in something of a consistent narrative so you can get a sense for the shape of the journey, and glimpse both a few moments that made a big difference as well as long, boring, arduous lulls in between.

That said, if you want to start a business, I actually don't know if you should copy me or not. I’m sure some of the things we’ve done should be repeated, some should be avoided, and for even more, the jury’s still out.

Still, I’ll make an attempt to tie cause and effect together without being fooled by randomness; ultimately, you must draw your own conclusions.

At best, you’ll find a useful lessons in here. At worst, it should be entertaining.

[Fleeing Como]

What was it like to start a business?

In the beginning, there was guilt.

Two days after we were able to start the business, I had a one way ticket to Europe to see the Olympics in Paris & vagabound.

Even before I left, I was conflicted: why was I going when there was so much work to do that, for legal reasons, I was unable to do for the last couple of months prior?

Still, I went off to Europe. I saw a couple of events at the Olympics, but found myself shipping code during a boxing match.

Maybe week later, I was sitting in an apartment in Como—I spent one day there coding for almost 12 hours.

We weren't making money, but I was spending money to be there.

Why? I could code for 12 hours from anywhere… and, some such places would be free.

I had a conversation with another founder on the phone, and he asked me the same question I was asking myself: "Why are you there? It won't increase your odds of survival."

So, I booked a flight out of Milan for a couple days later. Before I left, I enjoyed a swim in that brisk mountain water and a few last meals in the winding alleys, had a farewell tryst, and then flew home to live with my parent’s in Michigan.

[4 Months of no Revenue]

In the start, most of my time was spent coding or talking to prospects & beta users who we wanted to one day have as customers.

Lots of caffeine, not enough sleep.

Really, not much has changed, although now, the conversation are much more often with the people who are actually paying us.

My breaks were usually me pacing outside in my back yard, reading a book. I got into Asimov at the time, the Foundation books. Funnily enough, it impacted my engineering: the notion of 'magic' being the product of extreme and aggressively applied efficiency fascinated me.

I had a lot of hubris. The way I was engineering the product was not the way any one else I spoke with thought I should. It was a lot of "Why are you doing x yourself, you should pay for an API like y".

I ignored them: my hubris proved critical. A lot of our powerful features, like daily alerts, look a like accounts, and even our comparatively superior data quality, eventually came from the arrogance that told them no and myself yes.

Perhaps, de facto, the difference between unfounded and founded hubris is if you end up being right.

This was a period of intense focus, and much trial and error. On top of that, there was a lot of confusion and iteration & frustration. They all stemmed from expectations that were misaligned with reality.

We started in July, 2024. We thought we'd have $100K ARR by the end of the year. We didn't even get our first customer to pay us $100 until November.

[The First Customers]

At the time we started, Jack really began experimenting with LinkedIn content to see what would get attention.

In November, he had his first post go viral. It resulted in something like 100 people booking calls with us and me having 70 demos in 8 days.

Even after all of these calls, and dozens more the months before, we ultimately only closed 3 people for $400 MRR total, all of which took one or more follow up calls. The first came through at the end of November, 4 months after we started.

The way this timed out, I took over a hundred sales calls before we closed our first customer.

That's a lot of work with no reward. All of that is with over a hundred discovery calls in the sales space earlier in the calendar year.

I'm emphasizing this so much, because if you are starting a company and you talk to 10 or even 20 potential customers and nobody hands you their credit card, tough shit. Either I’m exceptionally incompetent, or you’re severely underestimating how much volume you need to do.

There are a lot of things that were holding us back, of course: I was bad at sales, I didn't have confidence in our product, people taking calls with us were often times just curious to see the new circus in town.

All of that starts to go away, with time and focused effort.

[The Danger of Listening]

Once we had our first few customers, we started getting a lot more information about what people thought they wanted us to build.

This is both a blessing and a curse. A blessing, in that you're no longer building in a vacuum, and you can see if people actually want the thing you have. A curse, in that a lot of people will want different things, and if you listen to all of them all the time, you'll end up with a Frankenstein of a product that's not so good at a lot of things rather than a product that is really, really good at one thing.

As we started listening to the people paying us more than the people who weren't paying us, the product began taking shape.

It became clear that we needed a lot more data than just what was found on a company's website, so we started adding in some social posts, news feeds, and SEC Filings. Rather than pay for APIs for all of this stuff, I wrote code at the end of 2024 to scrape a lot of this ourselves that is still running today with few updates and tweaks.

On top of that, Jack was iterating on our front end and we were trying out features like weekly and daily alerts, along with even finding people at the companies our clients were targeting.

Some of this stuck, some of this didn't. This is why more time with customers is a double edged sword, a necessary evil: both potential users and paying customers will tell you that you need certain features. Just because they say that and they give you a positive reaction when you show it to them, it doesn't mean they'll actually use it or that it's good for your business.

I think this is especially true very early; in January of 2025, I think we had a couple thousand dollars in revenue, maybe three. That's not a whole lot of people paying us a lot of money, but it’s far more attention and opinions than we’d had before.

[Creeping to $100K]

The first half of 2025 was a lot of iterating on both the front end and the back end. Going from MVP code that worked to something that would be more scaleable and wouldn't break all the time.

This is crazy to say, but in January 2025, I was still running prod as a bash script that opened tmux windows before I learned the joys of systemd & eventually ansible. I was beginning to realize how much I didn’t know about engineering and how much there was to learn and improve.

Jack had another viral post or two that resulted in more call marathons; win rates were still low, but they were improving.

We thought we'd hit $100K ARR in January; we didn't hit it til June or July, literally a year in.

Like closing the first customers, we were happy than we got here, but I wouldn't classify it as insane euphoria. Personally, it had this weird dichotomy of both coming later than I thought while also feeling like it was always inevitable when it finally did hit.*

_{*This is a strange contradiction, but it does characterize founders a lot.}

[Getting Opinionated]

Over the summer 2025, we made some decisions in rapid succession that together made our product & offering a lot more attractive:

• We doubled the unit price & raised the minimum

• We cut some tangential features, like any people data we had, doubling down on our core value prop of company level signals

• We got a lot more assertive & convicted on sales calls

• We qualified harder in our meeting booking, making people acknowledge price in advance

These decisions are an important piece of what we did, because a lot of it is so counter intuitive. We cut a feature everybody said they wanted (people data), we raised prices, and made it harder to talk to us.

I think what happened is that we came across as a lot more mature than we did before; it’s hard, when you’re just starting, to confidently say no to anything at all. But, when you do it, people respect you more & take you more seriously.

Ultimately, this triggered a big growth spike coming off the summer into the Fall. October in particular was an amazing and exhilarating month.

Things were breaking, though; we were spending tons of time on sales calls and customer support and success. A champagne problem, truly, but a lot to deal with.

It was at the end of the summer that we started paying ourselves, and in the fall that I moved out of my parent's house to split a room in a hacker house.

[Consulting Ceiling]

Our constrained bandwidth revealed a product weakness - we often needed to give heavy support & coaching to the clients for them to get success with our product. To deal with this, we basically had two choices:

• Raise prices & commitment & get paid more for our time

• Keep prices low / lower them & automate more of the inputs we were doing

At first, we went with the former: we started selling quarterly and annual contracts with 4 figure monthly minimums.

At the time, we thought this was the best solve. When our product works, it really works. But to get it to work, there was a lot of configuration and tweaking and fine tuning, and then the customers actually had to inject it into a process.

We thought that by charging more and getting commitments, we'd have more time to help the customers really get success with the product.

I think this class of solve would have worked if we charged even more and formalized the process further: eg, for a quarterly pilot, make it $10K, not $3K, and require weekly calls with the decision maker & trainings and all that fun stuff.

If we did this, though, then the business would've been bound by man power. To add more customers, we'd need more sales headcount. We'd basically be giving ourselves a job or tying growth to hiring!

Regardless, we found ourselves in this weird middle channel where implementation required effort but the cost wasn't significant enough to make the counter party really commit to it; it was a lot of effort on our end that resulted in aborted deals, and we weren’t able to do enough volume.

We were making more money than we ever had, but we could see that we had given ourselves a ceiling.

[A Product that Sells Itself]

So, as I haven't shut up about since April, we decided to go the other way: lower minimum price, lower commitment, with a product that just works.

That last part is the hard part: a product that just works. When you’re doing product led growth, I don’t think it's enough to have something that in some conditions gets your client ROI with certain configurations; we're learning that you really, really need to make it fool proof and incredibly simple to configure and use.

That's what we've been grinding away at lately: we want any customer who is a good fit & buys on our site to get value out of WhiteWhale.

Jury's still out on how much work is left between where we are and where we want to be, but we're confident we can figure it out.

I tend not to be the sort of person who carries many regrets, but with the benefit of hindsight, I'll make two observations:

• Doing product led growth forces you to be a lot more brutally honest with how easy your product is to use, because you're not always gating access to it via a sales call / training / framing.

• Once you start developing a product that people can just buy, there are a LOT of automations and features that are table stakes for success. They take time and effort to identify and build out. Even moving at break neck speed, there is a lot of ground to cover.

So, part of me does wish we would've started the product led growth journey sooner; I would've been able to spend more time aggressively improving the product and less time on CS / sales sooner.

If you enjoyed my ramblings, I’m here on about startups, software, the future, philosophy, the West, and more, every Sunday - please subscribe!

[My Way]

I tell you this story now specifically because it is strange and unorthodox.

We didn't raise capital, we didn't get into a fancy incubator, we weren't born good at sales or marketing; hell, I was a very green programmer when we started, even if I have something of a natural inclination toward it.

It also isn't exactly linear and involves a lot of long and boring parts and mistakes, some of which we've corrected, some of which I’m sure I don't even realize we're still making. And, of course, we're still deep in the trenches; there are things I haven't shared yet on purpose, and other things that I don't even realize are relevant to share yet.

It's hand to hand combat, but at least at some point you get to start paying yourself.

I'm grateful for the opportunity to be here and fight these fights, and I'm grateful for everyone, including my parents & Jack, who has made it possible.

Even though I’ve interspersed My Way through this post, I don’t at all feel like we’re near the final curtain call; rather, I can't help but feel we're a few decisions and less than a hundred hours of intense work from coming to a close on Act I of the WhiteWhale story.

I’m quite excited for Act II.

Live Deeply,