Hey bootstrappers,

You’ll make thousands of critical decisions in your career – some of them life-changing. 

But have you developed a process for making those decisions? Perhaps you’re of the 20% of the population who avoid making them altogether.

Whatever happens, you can’t let indecision get the better of you. You learn more from a poor decision now than you would from a lifetime of hesitation.

I’m not suggesting you flip a coin but instead refer to your ultimate goal. Better decision-making starts with a clear vision of what you want to achieve – your true north, as it were. 

Then work backwards from that goal until you understand what to do in that moment and under those circumstances to achieve it. 

This week’s founders set clear, specific goals that have helped them stay true to their path. Read on to discover how those goals became profitable businesses.

Chris Roper

Managing Editor

To Prevent Sites Like Yelp From Stealing Leads, This Former Painter Built a Competing Platform

When classifieds giants like Yelp began charging contractors for access to local markets, Greg Spates built ServiceBookie to help contractors reach customers online at a lower cost.

Greg Spates spent 30 years as a painter and decorator, enjoying the exposure (and clients) that classifieds and review sites brought to his business. Yelp had helped contractors like Greg top the search results for a reasonable price, but in later years, Yelp turned from friend to foe.

Referring to Billion Dollar Bully and his experiences, Greg described paying for empty leads that wasted his time or that pitted him against competitors. Contractors were forced to pay sky-high prices to continue ranking or risk obscurity. The game was rigged, so Greg changed the rules.

“When a customer fills out the form to contact a professional on their platform, they send the form to your competitors too. At the same time, they still charge your business thirty-five to a hundred dollars for that lead. They steal your leads and then sell them right back to you.”

Wins 👍

1. Marketing using Facebook groups. Greg built a Facebook community of thousands of contractors like himself, all experiencing the same issues and looking for a solution.

2. Starting niche and then expanding. Although he focused on painters first, he discovered cleaners, pet groomers, and other contractors needed his services too.

3. Diversifying revenue streams. Greg writes Facebook ads for contractors and charges a subscription for those who want to create multiple webpages on his booking site.

Challenges 🤔

1. Restoring faith in classifieds. Greg has to persuade skeptical contractors that his marketplace isn’t just another place where they’ll get ripped off. Social proof is helping.

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Aim High for Best Results: How This Founder Quadrupled Revenue When He Put a Million-Dollar Target on His Back

Serial entrepreneur Mark Whitman was a silent partner in his content business until Covid struck – and then he decided to take the reins and see just how big he could scale it.

Mark Whitman had been building content sites for years before he decided to productize it as a service and market it to other companies. Only he didn’t have the time to do it himself, so after partnering with friend Marc Bromhall, he took a backseat while Marc handled the day-to-day.

After scaling to $250,000 per year in revenue, Marc wanted a change so the cofounders decided to sell. Then Covid struck. Mark’s travel interests were hit, and he decided the best thing he could do with his savings was buy Marc out and run the agency himself.

“By December 2022, I want the company to generate a million in turnover with thirteen full-time employees and 105 writers. I don’t have aspirations to build something much bigger than that – I want to be able to focus on my other businesses as well.”

Wins 👍

1. Productizing the service. Since SEO strategies are unpredictable and take time, Mark charged for outputs (like content), not results, leading to simpler client relationships.

2. Building a lead database. Using Capterra and G2, the cofounders compiled a database of over 30,000 prospects and used drip email campaigns to sell them their services.

3. Setting a stretch goal. Mark's million-dollar target has encouraged him to expand into services that have proven very popular with his clients.

Challenges 🤔

1. Scaling operations with growth. Mark had to screen over 1,000 freelancers to build his team of 100 writers to cope with surging client demand.

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This D2C Founder Earned Millions of Views Over a Piece of Wood. Now He’s Bringing that Wood to Stores Near You

It wasn’t million-dollar growth or righting industry wrongs that inspired Roee Dunkelman to start a business. It was making the charcuterie board a little more fun.

Roee Dunkelman walked down a Whole Foods aisle one day and a thought occurred to him. Wouldn’t those boring charcuterie boards be more fun in the shape of penises? A silly idea to some, but for Roee, it was an opportunity to sell a novelty item at scale through social media.

While working at Clearco, Roee spent all day talking to founders. Starting a business seemed like the right thing to do for this former finalist of The Great Canadian Sales Competition. He’d found the right product. Now all he had to do was market – oh, and find a supplier!

“I found a brand doing what I’m doing when I researched the market. But they weren’t leaning into it at all. They weren’t even taking advantage of all of the lines and puns and all that stuff. I thought I could do this better than almost anyone else and wanted to see if that was true.”

Wins 👍

1. Teaming up with Testicular Cancer Canada. Embracing the product’s risque design meant Roee could raise awareness of male cancers and collaborate with charities.

2. Launching on TikTok. Roee knew that TikTok reveled in novelty, and his penis-shaped charcuterie boards could go viral if marketed right.

3. Collaborating with influencers. With celebrities like Matty Matheson and Pitbull sharing personalized boards on TikTok, Roee’s sales skyrocketed.

Challenges 🤔

1. Pivoting to B2B. Social media sales only went so far and required a lot of work to stay on top of trends. Now, Roee focuses more of his attention on supplying retailers.

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