From 2016 to 2020 I co-founded and ran DataOne Innovation Labs. We started as a data services company and later built Shoppr.ai, a marketing analytics product for ecommerce brands. We bootstrapped the whole way, and the team was eventually acquihired by Whatfix.
I’ve written about how it ended. This post is about the middle, the years of building with no safety net, and what they taught me.
The first 10 customers are a different job
When we started building Shoppr, getting the first 10 customers was brutally hard. You have a product you’ve poured yourself into, and you can’t get it in front of the right people.
I spent hours cold emailing, networking, and reaching out to anyone who might listen. Sometimes someone replied. Mostly it was crickets. When thousands of other startups are pitching the same people, being good isn’t enough to be noticed.
But once those first few customers arrived, everything changed. Validation turned into momentum, and people started paying attention.
The lesson: the first 10 customers aren’t a sales problem you solve later. They’re the job. Plan for them as seriously as you plan the product.
I fell into the MVP trap
One of my biggest mistakes with my first product was spending too much time on features and not enough on talking to customers or marketing.
I kept thinking, “If we build this one extra feature, it’ll be a game changer.” Then another one, and another. Before long we had a feature-rich product and not enough users.
What I learned the hard way:
- Your first version should be embarrassingly simple. If it works, people will tell you what’s missing.
- Customers don’t care about your roadmap. They care about their problems.
- An MVP is about validation, not perfection. The sooner you have real users, the sooner you know if you’re right.
The better question is never “What else can we add?” It’s “What can we remove and still solve the problem?”
Founders are the customer success team
At Shoppr there were just two of us co-founders, so we were also the customer success team. We spent a lot of time chatting with users, and honestly, it was some of the most valuable time we spent.
I had learned this even earlier, selling mobile accessories online as a side business years before. In a marketplace with thousands of similar sellers, I started putting small handwritten thank-you notes in every package with a way to reach me. A lot of customers wrote back to say they’d buy again because of it.
In May 2020, in the middle of the pandemic, a Shoppr customer in Italy sent us some wonderful feedback. In tough times, a message like that is fuel.
The lesson: customers pay for the product, but they stay for how you treat them. When you’re small, delight is your biggest unfair advantage.
Hiring at a startup is a two-way test
Hiring was one of our hardest problems. Over two years I reviewed thousands of resumes and personally spoke to many candidates.
I always asked the same simple questions: Why do you want to work with us? What do you already know about us? Did you visit our website before applying?
Most of the time, the answer to the last one was no.
Mass applications without any research are a red flag anywhere, but especially at a startup, where every person shapes the company. My advice to job seekers hasn’t changed: researching five companies properly will get you further than blindly applying to fifty.
Founders are more resilient than investors assume
While building DataOne we met many investors, and plenty of the first conversations were with junior associates. Some were thoughtful. Some were openly arrogant, as if access to funding made them the expert on a business they’d never built.
Entrepreneurship is lonely. You’re building the product, the team, payroll, sales, marketing, and support, month after month, with no manual. We didn’t always get the idea or the business model right. But founders are resilient. Most of the time, we figure it out.
That experience gave me deep respect for investors who genuinely listen, stay approachable, and don’t hide behind layers of gatekeepers.
A related trap I see now: founders spend months polishing a pitch deck to convince VCs, but won’t spend a week building something to convince customers. Selling the dream of a product is not the same as selling the product.
A lesson I only understood years later
One of DataOne’s early clients was a well-known marketing leader, regularly featured in major business publications. We were building them an invoicing and client-management product for freelancers and agencies.
But what caught my eye was something else: they published three new blog posts every single day.
At the time I didn’t understand SEO, and I wondered why anyone would spend that much on content. Years later, building Shoppr, I went back to their website and finally got it. They ranked for thousands of keywords and had built a huge library of organic backlinks. Their blog wasn’t a cost. It was a growth engine.
The lesson: some of the smartest strategies look wasteful until you see them compound.
A strange postscript
Years after DataOne was acquihired, I got an employer verification request for someone who claimed to have worked there. I had never heard of them. Then came a “relieving letter” with our logo and address, and a link to a website that was a near-perfect clone of our old one.
I reported it to the Cyber Crime Portal. It was a strange reminder that a company’s name can outlive the company, and that background checks matter even more than we think.
What I’d tell a bootstrapped founder today
- Treat your first 10 customers as the real product launch.
- Ship less. Talk to customers more.
- Do customer support yourself for as long as you can.
- Hire people who did their homework on you.
- Respect the long game. Content, relationships, and reputation all compound slowly, then suddenly.