Hey bootstrappers,

How did you imagine adulthood?

A straight line from school to college to job or business?

Many of today’s societies push that narrative. You work hard at school to later graduate college and slide into a lucrative career. 

While that old formula might’ve worked years ago, in the US, 68 percent of workers believe you find more security doing things your own way. 

Take this week’s founders, for example:

• A car mechanic in a “dead end job” who’s now a podcaster earning six-figures
  
  
• The students whose “crappy site” became a multimillion-dollar shipping business
  
  
• A digital marketer who left the “hamster wheel” to become a strategic storyteller

Whatever lane you’re in right now, it’s never too late – or early – to switch and find success in doing what you love. 

Trust your gut and go for it. 

Chris Roper

Managing Editor

Ed Lynes, a college dropout, should've been happy, but his agency created nothing but disillusionment. Only when he switched to strategic storytelling did he finally feel free.

Pivot or Persevere? How This Founder’s Change in Direction Doubled His Agency’s Revenue and Headcount

Ed Lynes never imagined digital marketing to be such a slog. His team churned out reams of content and worked long hours to hit arbitrary targets, and clients still pushed prices down. With employees leaving regularly for better work, Ed was left to pick up the pieces.

Only when a disgruntled client explained what Ed was doing right did he realize it was time to switch lanes. His company would shift away from digital marketing to strategic storytelling, a niche that doubled its revenue in 2021.

“Digital marketing was much more profitable, but the work sucked. We weren’t happy. We looked at the [strategic storytelling] side of the business, and although it had fewer clients and less revenue, it felt more meaningful to the whole team. It also had a bigger impact for clients.”

Turning points

1. Choosing happiness over money. Ed’s story is a classic example of money not making you happy. His pivot created the conditions for success without caveats.

2. Asking an unhappy client for feedback. Ed discovered what was wrong, but better yet, what was right, giving him the impetus to focus on it full-time.

3. Applying storytelling principles to his new business. Ed needed to consolidate Woden’s new business model with a story his team could get behind.

Ryan Sullivan's dad asked him to give up podcasting and get a “real job”. After a disastrous corporate role, Ryan dug in his heels and founded his own podcasting company.

How This Former Mechanic Launched a Podcast Incubator Bringing in Six Figures and Growing

Ryan Sullivan started his first podcast as a hobby. In the day, he’d slide under cars to fix engines and change oil. At night, he’d rap and interview local musicians and entrepreneurs about how they changed their lives and livelihoods.

Realizing he had more fun in the evenings before a mic, he quit his day job and advertised his services on Upwork. Unfortunately, it didn’t pay off. After a failed corporate job took its toll on his mental health, Ryan decided to turn his love of podcasting into an agency that helps others.

“If you have a company that sells B2B marketing and one of them has a podcast and one doesn’t, you’re going to go with the one that has a podcast because people will quickly trust that company more because they can hear them and how they interact.”

Turning points

1. Giving up his day job. Although it was a slow start, Ryan might not have built his business had he not had the courage to pursue what he loved full-time.

2. Trying a corporate podcasting role. Ryan learned how to produce a podcast from beginning to end, and although it didn’t work out, he left with skills he could easily monetize.

3. Helping others do podcasting. Rather than monetize his podcast, which might’ve taken years, Ryan chose to sell his podcasting skills to others, resulting in big profits.

While studying for finals, Nick Malinowski and Parker Barnes took part-time jobs that gave them insight into logistics – and a business idea that would make them millionaires.

How to Start a Seven-Figure Ecommerce Warehousing Business: Find Small Clients and Make Them Big

Nick Malinowski and Parker Barnes started a logistics business while still in college. The idea was to do order fulfillment for smaller businesses that struggled to secure warehousing. They started with a basic website and then secured some warehouse space with their first client.

After marketing their services on social media and every online forum they could find, clients ate up their offer of “buy now, pay later” postage. As they scaled, juggling warehouse management and studying for finals, the duo’s biggest challenge was finding the right labor at the right cost.

“Labor costs are the main pain point for a 3PL. Robotics is becoming very common, but until now picking an item is too complex for robots to handle. Some are fragile and some are squishy. I can see the way warehouses look and work changing dramatically in the future.”

Turning points

1. Focusing on forum marketing. According to the founder, this delivered more warm leads than social media and still brings in leads today.

2. Investing in the hiring process. When a warehouse manager got arrested, the cofounders created a better system for finding and evaluating staff.

3. Using contractors to keep costs low. The cofounders hire contractors for busier seasons and only ever use free applications rather than enterprise alternatives.

Advice of the Week

“It was certainly a gamble to cut off all of our recurring revenue at the time. But I do believe that if you work on something you’re passionate about and it gives you purpose, you have to trust that it will work out. I thought: If we believe in it, it’s worth doing 100 percent.”

 - Ed Lynes, Woden

If you've got a great story about your bootstrapped company, we want to help tell it. Fill out this form and we'll be in touch soon. 

What did you think of this week's stories?