Hey bootstrappers,

They say you find out who your friends are when times get tough.

I’m not sure about you, but the saying rings true for me. A friend I seldom speak to has always been there when things hit the fan while others ran for the door. 

Call me naive, but I think most people, even those you’re not close to, want to see you succeed. The writers and I, for example, are all rooting for you (and we’ve never met you before). 

When you’re stuck with a problem you can’t solve, do like this week’s founders and turn to communities for help. Your peers, colleagues, mentors, and even customers can pull you out of your darkest moments. 

Happy Spooktober. 🎃

Chris Roper

Managing Editor

How the Power of Community Helped This Founder Publicly Quit His Job on Twitter and Launch a Six-Figure Startup

Damon Chen missed the office camaraderie when Covid sent him home. Feeling isolated, he built a video-sharing app to reconnect with his peers that transformed into video testimonials.

Lonely in lockdown, Damon took some unpaid time off to reflect on his future. He loved tinkering with various projects, and while interacting with entrepreneurial communities online, he built Lonely.dev (now Testimonial) for founders to share videos of their products and get feedback.

The site was popular with indie hackers, and as Damon’s unpaid leave ended, he challenged himself publicly to monetize it. If founders enjoyed sharing feedback this way, perhaps customers would too. Damon promised Twitter to quit his day job if his gamble paid off.

“I started to ramp up my non-technical skills like marketing, sales, and customer support. Now I talk to my customers every single day. Knowing what they truly need and making it happen is such great satisfaction.”

Wins 👍

1. Simplifying onboarding. Damon had listened to founders complaining when products required coders to deploy, so he recorded simple tutorials that anyone could follow.

2. Quitting in public. Holding himself publicly accountable for the success of his business helped Damon stay focused on his goal of hitting $1,000 in monthly recurring revenue.

3. Community marketing. Damon’s business has grown through affiliates, referrals, and testimonials of Testimonial on Testimonial (say that in a hurry) – at little cost.

Challenges 🤔

1. Lifetime pricing. After launching Testimonial for a lifetime fee, Damon quickly realized he needed to switch to a recurring revenue model or risk never making any money.

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A Lesson on Income Diversification From a Founder Who Lives By the Rule

Ali Baghshomali asked Mixpanel, a product analytics vendor, if he could teach its customers how to use Mixpanel products, and today, it earns him six figures in revenue.

When serial entrepreneur Ali Baghshomali’s first startup failed, he joined Buzzfeed as a data scientist. During that time, he learned that data skills are universal, but few departments possessed them. He wanted to launch a data school to help but didn’t have the funds.

Ali left Buzzfeed and joined Bird (an EV company) only to be sent home during the pandemic. He began consulting for various companies, finally earning a Mixpanel certification that led him to found a new startup – data analytics coaching for Mixpanel customers.

“I completed Mixpanel’s certification program because I figured the official badge on my site would appeal to more [freelance] customers. I did well on their program, and Mixpanel liked my data background. So, they started sending clients my way as one of their trusted partners.”

Wins 👍

1. Delivering exceptional service. Ali admits that competing with bigger training firms was only possible because he provided a hyper-personal and specialist service.

2. Building an online data school. Ali’s clients are ideal for the data school, and as it’s asynchronous training, it provides Ali with more scalable income.

3. Bootstrapping. Without investor funding, Ali has stayed in control of his work and schedule, and even donates a portion of profits to charity, which his clients love.

Challenges 🤔

1. Specialization. While it got Ali’s business off the ground, specialization became a bottleneck. He overcame it by hiring and training staff in other analytics products.

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How the MicroAcquire Community Helped a Struggling Founder Save His Business

Julian Lumpkin was out of options when he listed his startup, SuccessKit, on MicroAcquire – but instead of offers, he got advice that helped turn his business around.

Julian started SuccessKit to help salespeople close deals using customer testimonials. Despite the best salespeople always using customer success stories when pitching, the practice was far from ubiquitous across teams. Julian saw a business opportunity, and sales reps agreed.

But after building an app for collecting these stories in one place, Julian struggled to sell subscriptions. He didn’t take a salary for a year and the business barely broke even. Deflated, he turned to MicroAcquire for an exit but discovered how to solve his growth problems instead.

“Those [buyer] conversations motivated me to continue. They taught me the importance of content marketing – tutorials on writing case studies and so on. Knowing what a potential acquirer would do helped me understand where the growth levers were.”

Wins 👍

1. Pivoting to services. Offering bespoke case study services (such as writing and design) helped buy Julian runway when the platform floundered.

2. Listing on MicroAcquire. At his lowest ebb, Julian believed he had no way out. The MicroAcquire community taught him otherwise and now his business is thriving.

3. Educating his prospects. Switching to content marketing helped zero in on the customer problem: Customers wanted to write case studies, and Julian taught them how.

Challenges 🤔

1. Starting as a product business. Julian couldn’t compete against VC-backed tech companies that had the funding to execute fast and often, but he could on services.

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