From Bootstrapped Launch to Exit
In August 2021, Yaakov Karda and his co-founder signed an acquisition agreement to sell Chatra, the profitable live chat platform they had spent six years building. For Karda, the sale capped a longer journey that began with his first startup, Getwear, which shut down after a six-year struggle. Looking back, he says, the path from failure to exit yielded lessons that go far beyond the mechanics of a transaction.
The Value of a Long-Term Partner
Karda credits much of his success to continuity in partnership. His co-founder was a childhood friend, and the two had worked together since their days of less-than-legitimate high school side hustles. When Getwear crumbled, that bond was the reason they stayed together and launched Chatra rather than going separate ways.
The trust built through early struggle, Karda says, proved essential when navigating the stress and inevitable disagreements of building a second company. Having a partner you trust along for the ride made the difficult moments manageable. The collaboration was too valuable to abandon just because one venture had failed.
Rebuilding With Different Ambitions
After a first startup fueled by ambition and, eventually, failure, Karda and his partner approached Chatra with a more modest goal: build a simple, sought-after product that pays the bills. The company was bootstrapped, which meant a small, fully remote, independent team. In 2015, that was a novelty, and a decided departure from Getwear’s larger operation with an R&D department and a production office in Mumbai.
They chose their next market by looking for an intersection between what the market needed and what they already knew well. Customer support was an obvious fit, since Getwear had relied heavily on live chat and the pair had already built an internal tool for conversational communication between their Mumbai factory and customer-facing teams. That internal product was built on an obscure framework with real-time messaging out of the box, giving them a foundation of expertise.
The market was crowded — roughly 20 established competitors in 2015 — but Karda didn’t see that as a deterrent. He reasoned that if 20 products could do business, there was room for a 21st. He came to treat competition as market validation rather than an obstacle and now says confidently that competing in a crowded market is entirely possible.
The plan wasn’t to innovate something altogether new. While Getwear had been deeply original, Chatra sought to improve a known category by borrowing features and design standards from elsewhere. The live chat platforms of the time felt dated, with clunky Windows 95-era interfaces, poor user flows, and lost conversation histories. Slack, Facebook Messenger, and Telegram had set new expectations for messaging UX. Karda and his team used those products as a blueprint for a modern chat widget and agent dashboard.
A product does not have to be new to redefine and disrupt a market. It’s possible to lead by introducing modern standards and designs rather than coming up with something radically different.
A Lean Path to Market
The bootstrapped reality drove two decisions early on: launch and earn immediately, in months rather than years, and don’t spend on paid acquisition, brand awareness, or an outbound sales force. That pushed Chatra toward small businesses that could onboard via self-service with fewer features required.
For marketing, that meant growth hacking, the favored term in 2015. Chatra had a natural channel: a “powered by Chatra” link displayed in the website widget. But the link would only be useful once there were enough customers using the widget to see it.
To build that initial base, Karda and his team combined web scraping and email discovery with cold outreach. Their first instinct was to mine their competitors’ customer lists, but that backfired. Angry recipients complained directly to competitors, and the CEO of one prominent live chat company demanded they stop contacting his users — and asked for a donation to a civil liberties NGO, which they made.
Instead, they redirected cold outreach toward e-commerce website owners, automating lead research, email sending, and reply handling at massive scale on a small budget. Cold outreach turned out to be the single most effective marketing tool they ever used, and it wasn’t reserved for enterprise sales.
When the user base grew large enough, the widget link took over as the number one acquisition channel. Karda calls that a viral engine of growth — existing customers generating leads without any further effort. Getting there, he says, is often murky and unreliable, but the path can be planned and tested. He notes that small details make a difference: changing the link text from “Powered by Chatra” to “Get Chatra!” produced big gains with trivial effort.
Content marketing was a separate experiment aimed at filling the top of the sales funnel. The team produced well-researched books and guides, but the effort failed to attract meaningful new leads. Karda’s conclusion is not to avoid quality content, but recognizing it as a slow-burn channel, not a near-term growth strategy.
Churn, Pricing, and the Real Value of Customers
Once Chatra had reached product-market fit and was growing organically, the focus shifted to the numbers that matter in a subscription business: churn and customer lifetime value (cLTV). Long-term subscribers generate more revenue than new ones cost to acquire, so keeping churn low became the central problem.
We found it useful to separate churn into two categories. Avoidable churn is something you can act on. The other kind—natural churn—is not your fault. If a small e-commerce store closes down, it stops paying for your service. That is simply the reality of the market, and no retention strategy will change it. You just have to live with it.
Chatra’s pricing was modest, but the cLTV was high. Many customers stayed for years. That high lifetime value justified spending more on customer acquisition, which we did by running paid ads in the Shopify app store. The ads improved our search position, and we held onto a top spot in our category. Looking back, I believe that strong positioning played a meaningful role in Brevo’s decision to acquire us.
We did try to convert active free users by offering them a full year of the paid plan for one dollar. The result was surprising: almost nobody took the offer. That experiment led us to a blunt conclusion: there are customers who will pay and customers who will not, no matter what you do.
Pricing experiments were even more counterintuitive. We raised the subscription price from $11 per seat to $19, and the conversion rates barely budged—both from visitor to user and from free to paid. In a freemium model, it turns out the price matters far less than founders tend to believe.
To grow revenue per customer, we also launched additional products. Livebar delivered in-browser notifications for recent purchases, and Yeps provided a simple sticky announcement bar for webpages. Both were solid products technically, but neither gained traction with our existing audience despite prominent promotion. Selling a second product to a loyal customer base is not automatic—that assumption cost us time and money. We eventually shut down Livebar and sold Yeps for a price that barely covered its development and support costs.
The Decision to Sell
Chatra ran lean. With viral growth and self-onboarding, the engine ran almost unattended, giving us founders both income and time. We had stopped thinking about an exit long before, so most acquisition offers that arrived were easy to ignore—the best one we received was a valuation of 2.5 times our annual recurring revenue (ARR), which was far too low.
Then came an email with a different tone. The details were vague, but we agreed to talk. I told the buyer we would not consider anything below the venture-backed SaaS standard—around eight times ARR at the time. The reply caught me off guard: “Let’s talk. Are you ready to sign a non-disclosure agreement?”
My main hesitation was the risk the acquisition posed to the team and the product. I did not want to abandon customers who relied on Chatra. The buyer addressed that concern directly, promising Chatra would remain a separate line of business, no jobs would be cut, and they would fork rather than shut down the product—at least initially. Even so, the thought of letting go made me want to walk away from the negotiation at times.
Why We Went Through With It
We had three reasons to sell:
- Stagnation. The company felt stuck in its mature phase, and we missed the energy of building something new.
- Risk diversification. We knew that the good times would not last forever, and relying on a single revenue stream felt unwise.
- Pride. I wanted to go through an acquisition at least once—it felt like a rite of passage for an entrepreneur.
Chatra was profitable and growing, but we had little left to do as founders. Moving upmarket to compete with Intercom and Drift was never attractive. Our niche felt comfortable, but it offered no room to expand. We were at the end of the road.
Timing worked in our favor. Shortly after the acquisition closed, the market took a serious hit. If we had waited two more years, we would never have received an equally generous offer. That said, I still wonder what would have happened if I had asked for more. The buyer was not short on cash, and a higher number would have been meaningless to them but very significant for us.
The Payout Structure
Every acquisition looks different on paper. Ours had three components:
- An initial fixed payment at closing;
- Flexible payouts tied to post-acquisition milestones;
- An escrow amount held in case of legal claims or other problems.
We assumed that structure was final and never tried to shift more weight into the initial payment. In hindsight, that was a mistake. Accepting a large deferred payment effectively gave the buyer an interest-free loan and left us exposed to uncertainty. We should have negotiated harder—it was the last time we had any leverage over the deal.
The Real Takeaway
Letting go of Chatra was hard. The team had become my second family, and I felt close to every line of code and every pixel we shipped. I still feel the nostalgia. The financial freedom, though, has been worth it.
The acquisition itself did very little for my personal well-being or self-worth. What stuck with me is a much simpler idea: success is the process of doing things, not a destination you reach. I am not sure where this journey goes next, but I expect there will be another business challenge ahead, along with a chance to help others who are just starting their own founder journeys.
