Hey bootstrappers,

Back in the early 2000s, I took a telesales job to pay my way through university. 

It’s probably the toughest job I’ve had. Long hours repeating a script to people who didn’t want to listen. Those who racked up sales never failed to impress me. 

What was their secret? They answered all objections, stayed positive every shift, and turned on the charm like their life depended on it. 

The right sales skills in your business can help it survive in even the most competitive markets. If you’re not a natural salesperson (like me), consider hiring someone who is. A dominant trait of serial entrepreneurs is that they excel in persuasion, a tactic critical in sales. 

Read how this week’s founders learned how to sell below.

Chris Roper

Managing Editor

PS One of our in-house journalists, Peter Upton, will take over newsletter duties next week while I'm on vacation. Give him some love. 😊 

How to Change the Online Gambling Industry From the Inside: Bet On Better Affiliate Marketing

Former professional gambler John Wright built Statsdrone to help gambling affiliates make better ads while still being ethical – but his first attempt to sell the platform fell flat on its face.

John applied his analytical mind to iGaming in his final year of university. When he made more than he could as a fresh engineering graduate, he eschewed a traditional career to become a full-time gambler. If he failed, he could always fall back on his degree.

Soon, he discovered an affiliate industry built around attracting new gamblers to the table. Most of them prioritized the wrong things, so he developed an ad-tracking system that optimized ads and addressed the elephant in the room: gambling addiction. But would affiliates buy it?

“I thought it would be a walk in the park. Some friends took six months to respond, and I received every type of rejection you can think of. I needed a way to have an answer to every question before they asked it.”

Wins 👍

1. Recognizing an industry-wide problem. Many affiliates were incentivized to bring in problem gamblers, which seldom delivered the sky-high commissions on offer.

2. Switching from B2C to B2B. Rather than launch an affiliate site (B2C) in a saturated market, John wanted to target affiliates (B2B) as there was much less competition.

3. Hiring a corporate cofounder. John lacked ops experience, so he hired a corporate cofounder first who knew how to manage HR and teams.

Challenges 🤔

1. Transforming an industry. Since casinos win when people lose, John has spent much of his earnings helping gambling addicts recover funds and building a free casino blocker app.

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Walk a Mile in Your Customers’ Shoes: How This Founder Went From Owning a Gym to Building Tech for Gym Owners

After working his way to the top of the gym industry, John Franklin acquired a web agency and now specializes in giving gym owners everything they need to succeed in a competitive market.

John Franklin used to own five gyms in NYC. During that time, he learned that you must be an exceptional marketer to get bodies through the door. When a mentor recommended he buy a web agency, he was hesitant at first but relented because he wanted to help gym owners succeed.

Gyms sold, John and cofounders Mateo Lopez and Kaleda Connell turned the agency into an all-in-one SaaS platform for managing (and maximizing) gym memberships. Their sales strategy was to acquire clients cheaply (leveraging networks) and upsell them a subscription.

“Many of these customers knew us from the coaching group. Since we were active and well-known members, we built a lot of trust and proved our expertise over the years. People believed us when we said we had something that would work better for their businesses.”

Wins 👍

1. Interviewing the agency’s customers. John and his cofounders built a platform that solved gym owners’ pain points because they’d invested time in learning them.

2. Being fast when others were slow. Launching a new web agency during the pandemic meant they could build websites quickly while the competition was backlogged with changes.

3. Turning down clients to maintain stability. Building websites that would convert and always run well meant saying no to clients who wanted full website permissions.

Challenges 🤔

1. Earning his battle scars on main street. John believes he wouldn’t have been as successful had he not lived (and learned) through the tough NYC gym market.

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After Losing His Dev Team to a Malicious Investor, This Former Analyst Now Helps Retail Investors Beat the Markets

Amrit Rupasinghe had already built one app, one agency, and began working on a third when a rogue investor finally forced him onto a new path: helping people pick better investments.

Amrit had thought he’d seen the back of his financial analysis days when he launched his first startup, Buzzbird – a social networking app. But after failing to monetize the app early enough, Amrit switched to recruiting Sri Lankan devs for American companies. Then disaster struck.

One of his early investors poached his team, forcing Amrit to wind down his agency and look for a new business idea. Americans clamored for investment advice after receiving Covid stimulus checks. Could Amrit help them pick stocks using his industry knowledge?

“Many people, including my friends, were badly burned by the markets and I thought I could help. If a hundred million people go to Yahoo! Finance every month for stock picks, I thought, ‘Why can’t I find the 700 best stocks on the markets for people too?’”

Wins 👍

1. Launching a beta with friends and family. Early feedback helped refine his product for public consumption.

2. Publishing his product for free in investing communities. A staggered launch across ringfenced communities helped confirm demand before going public.

3. Launching an affiliate program. The battle for better investing took place over social media, so Amrit partnered with well-known influencers to get his first paid customers.

Challenges 🤔

1. Doing two jobs at once. Amrit still contracts during the day to make ends meet while growing Wall St. Rank in his spare time. He’s recently taken on a trusted CTO to help.

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