Hey bootstrappers,

Have you heard the myth that it takes money to make money?

It bothers me for two reasons.

First, it ignores the influence of hard work. And second, it implies to get the right product in front of the right people, you need investment, which just isn’t true. (Time is often enough.)

But if you need a little cash injection to get your business off the ground, consider the tactics this week’s founders used. 

1. Start your business as a service so you can charge from day one. Automate later.
2. Sell one business, perhaps a smaller hobby project, to fund a bigger one. 
3. Offer a basic product first to generate revenue you can reinvest into upgrades later.  

There are plenty more tactics to choose from, including using freelance or day-job income, but the important thing is to get started. 

(Did you know that even hobby or practice projects sell quickly on MicroAcquire?)

Chris Roper

Managing Editor

These Founders Defied the Advice of Their Peers and Built a SaaS to Give Their Customers More Autonomy

Brothers Chadwick and Darton Rose reinvested the earnings from their data consultancy to launch a SaaS business that helps businesses collect and analyze their data independently.

Chadwick, Darton, and their friend Philip Rose cofounded Treehouse Technology Group with a simple mandate: help small businesses turn their data points into actionable growth strategies. As their expertise helped companies unlock better insights, an unexpected problem appeared.

Without TTG’s oversight and assistance, small businesses couldn’t figure out how to use their analytics software, which was often complex and expensive. Rather than coach them long-term, the cofounders built InsightOut to bring their data sources under one intuitive dashboard.

“I envision a world where you’re plugging into Salesforce and our system tells you exactly what to pay attention to and deciphers your data automatically. Many analytic tools are built and then abandoned. But our users look at the data first thing in the day and again before they leave.”

Wins 👍

1. Adapting to cultural expectations. Rather than irk the companies they wanted as clients, Eric and Manami removed the reviews section to avoid alienating prospects.

2. Creating a single source of truth. Rather than force founders to re-learn a new application, InsightOut integrates with existing software to simplify data analysis.

3. Charging a monthly subscription. InsightOut’s monthly recurring revenue grew so quickly that the founders no longer needed to siphon funds from its parent, TTG.

Challenges 🤔

1. Simplifying complex software. To accomplish their vision, the cofounders relied on Gary Stanton, TTG’s VP Technology, and his background in art and design. 

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Would You Rather Be the Biggest SaaS in Italy or the Biggest in the World? 

Italian entrepreneurs Luca Micheli and Daniele Ratti were high on the success of two acquisitions when they launched Customerly to worldwide acclaim.

MBA study buddies Luca and Daniele learned an important lesson from building their (now acquired) businesses: When customers struggle to navigate SaaS UX, signups fall and support requests rise. They formed Customerly with Matteo Martinelli to solve the problem.

Customerly is a chatbot and CRM that guides customers through those important early experiences of a new application. Today it’s one of the best live chat applications globally, with 10 million customers per day. But it’s taken several years and rethinks to get right.

“Now we have many different clients from solopreneurs to enterprises. Each has its problems. Every time we build the next feature, we need to decide which customer type is more important. On the other hand, we’re fortunate that we get to speak to people in so many industries.”

Wins 👍

1. Beta testing at scale. The cofounders tested Customerly using business contacts they’d made while building their previous apps, some of which had 200+ customers.

2. Adding live video chat. When signups fell during the pandemic, the cofounders tripled MRR by adding video chat to help businesses connect with people in lockdown.

3. Deploying in-chat surveys. Customers give product feedback while using the app, which is quicker and gets more responses than an emailed survey, for example.

Challenges 🤔

1. Moving to Ireland. Luca left Italy to incorporate Customerly in Ireland, hoping it will eventually help the business get acquired.

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This Founder Quit Google to Help Others Land Their Dream Jobs

Feeling emotionally unfulfilled, Stephen Cognetta quit Google to travel the US while coaching from his van. Later, it would become Exponent, a mentorship marketplace earning six figures.

Stephen has always enjoyed helping people, whether coaching them for interviews at the US’s biggest tech companies or volunteering at a suicide prevention hotline. Moving into mentorship as a business seemed like a natural move – but it didn’t start that way.

Leaving a lucrative and rewarding job at Google, Stephen got in his van and drove across the US in search of inspiration. He coached on the road, initially to fund his travels, but it eventually snowballed into a mentorship, education, and recruitment program for tech candidates.

“Exponent takes a practice-based learning approach, which we’ve found far more helpful than existing methods. We created content that covered the whole funnel, from the structure of an interview to frameworks for answers to how you should conduct yourself.”

Wins 👍

1. Writing about his coaching tips. Stephen’s unique insights into tech recruitment attracted a wide audience that would later become his first customers.

2. Selling short courses. To test the market, Stephen packaged up a few resources and sold them to his readership at $8 each – many bought and wanted more of his help.

3. Enlisting expert mentors. Exponent matches mentors in specific fields to candidates, creating a bond that helps candidates learn and can also lead to placements.

Challenges 🤔

1. Working while on the road. While it gave him the space to chase his dream, coaching from a van was difficult due to spotty internet and cell service.

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