Examples of 3 Entrepreneurs Who Bootstrapped $1M Businesses

Many of us love the underdog story, and we love the many inspirational stories behind entrepreneurs who made it. Especially those who fought many battles and hit the coveted $1M mark. These are the entrepreneurs that we learn from and we pass on.

The rags-to-riches story, the business tycoons and the strong and brave, all make us work that much harder and faster in our lives. We want to find the edge and we fail to remember some of the valuable lessons. But what we do remember are the stories that drove them to where they are.

The founders listed here are the ones who couldn’t raise money from VCs but didn’t’ stop there. They went on about their business and bootstrapped until they could raise enough money. As compelling as that sounds, bootstrapping is insanely difficult.

However, many do it daily. It’s a tough task to cut costs and work out of a garage, but some of the biggest brands in the world started out that way. Fewer deals are being made in 2018 as well. While we’re only a few months past last year, already VCs are only betting on big safe investments. Deals are falling by more than 5% yoy, and that’s not a great sign if you’re an entrepreneur looking for capital.

This is where the hero’s journey is so important. When we can understand how self-made entrepreneurs and founders can make dreams into million-dollar businesses, we take notice and learn more about them. Their success teaches us valuable lessons and we each take away something unique to our own existence.

When we have the right set of balances of risk, reward, confidence and competition, we can earn more than we have ever imagined and produce results for the clients and customers we work with. Best of all? None of these three founders had to cheat, lie or steal to get ahead. They got ahead with hard work, dedication and putting in the hours necessary to win the deal. Here’s their journeys –

The startup that didn’t even know what VC was - Markus Frind

There are some stories that come along, that truly touch our hearts in meaningful ways. This is the story of Plenty of Fish, which had a dating service launched by a solo founder. It's not a common experience for most entrepreneurs to do things solo, as VCs love to see co-founders with complementary skills. He started the website in 2007 and by 2015 he ended up selling for $580 M.

So, what did he do to skyrocket his dating site?

First of all, he learnt how to code the basics himself. He didn’t know how to design a website or app in ’07 and learned how to do it by his own curiosity.

He launched the app in 2007 and he was surprised to see that he was doing better than Match.com (a behemoth at the time). His idea was just better, and his app ran faster than the competition. In 2008, the site made $10M that year. It was a great matching algorithm and it worked like a charm.

What was so unique about his journey?

His attitude was so unique. He didn’t enter the office until 10 am, and he never really like going to work in the first place. He would accomplish everything he needed to in the first hour of the work day. He made sure that the site ran itself and needed no management to check on it daily.

He built the website purely on word of mouth and with no advertising whatsoever.

Four serial entrepreneurs, a strong history of success - Dan Engel, Ken White, Jason Foodman and Ryan Dewell

These guys had a lot of experience getting from point A to point B, and they did it with the learnings that they had acquired over years of building successful businesses.

All four of these guys had experienced success with previous start-ups. This of course, gave them a leg up when it came to launch Fast Spring and the subsequent challenges that came along with that. They had a vision that they wanted to see through and had knowledge and confidence to execute it.

FastSpring was the go-to company for merchandising, ecommerce and fulfilment solutions. It was selling digital products in 2005, and the only money they had was the $30K that the four of them could muster up. Money wasn’t the issue for them though.

They didn’t care if they weren’t working or living in the best of situations. They wanted to reach their revenue, profit, and headcount goals to know for sure that they had arrived.

They split the load equally and worked together to create something unique and bigger than them. They took no salaries, sacrificed their time, and started burning through their savings. They were constantly on the go and finally built a business that could stand on its own. They took capital in 2013, and grossed $45M in revenue.

Bootstrap, bootstrap, bootstrap to grow cash - Connor Gillivan

When you stick to your principles of bootstrapping, you become an entrepreneur who’s successful in building million-dollar companies. He’s written a book about it – Free Up your business. He started a company on his own, without outside investment and working hard for years.

FreeUp, his business is a multimillion dollar hiring platform that serves 2500+ businesses around the world. Even though the business has grown over years, he’s still stuck to his principles of bootstrapping and scaling.

Bootstrapping wasn’t easy for Connor, and it’s the right way for him. It took determination, struggle and vision for long-term success, but he’s stuck by it. In fact, he swears by it – entrepreneurs need to understand that bootstrapping is your friend.

Conclusion

When it comes to learning from the best, you can learn from stories across the world. These stories fare well when you look at it from a distance, but when you’re living through these bad winds, you don’t see it clearly. This is why stories are key to learning more.