Tom Shea’s startup recently raised a huge $600 million fundraising round. It’s not his first rodeo either.

During our time together on the DealMakers podcast, Shea discussed when you should make the leap to starting your own business, bootstrapping your startup from zero to a $50 million exit, raising massive financing rounds, getting to scale, taking on some of the largest tech companies in the world, and making your brand the standard.

Listen to the full podcast episode and review the transcript here.

Born in Michigan

Tom Shea was born and grew up in Michigan. It was when Detroit was the center of the universe, and GM had ruled the number one spot on the Fortune 500 for 75 consecutive years. 

Of course, now they have been eclipsed by disruptors like Uber which are valued many times higher. 

His father was an entrepreneur who lived through the trials and tribulations of being a business owner. He advised Tom to take the traditional route and go to school and get a corporate job. 

Tom went to college to study finance and accounting. Then he landed an internship with one of Motor City’s big giants, Chrysler. During the day he was working in corporate finance, on the path to becoming the CFO of a large company. During his free time, he was writing software and programming, and even selling some of his own work on the side. 

This period gave him the experience in understanding how big companies work, managing their finances, and witnessing their challenges first hand, as well as balancing that with what he was talented at and passionate about.

“If I can go kill it, clean it, and cook it, why am I doing that for somebody else?”

If you can do all three of those things, why would you be paying someone else for your meals? When it comes to business, Tom says, “if I know how to find the deal, get the deal, sign the deal, I think I might have a fair chance here of becoming an entrepreneur and being successful myself.”

He had been doing some consulting and saw where his experience in both software and corporate finance apexed. 

Consulting provided a chance to further test the waters and get experience in creating a product, selling it, and delivering it, with the reduced risk and safety net of doing it under someone else’s umbrella first. 

Then together with his best friend and brother-in-law, Shea co-founded and brought his first company, UpStream Software to life. 

Bootstrapping to $50M

They started out with the mission that every customer would recommend their company, product, and services. A model of building a business one customer at a time. He says the logic is that “if I can get one customer to pay for my product or my service and be happy with it, then I probably have a pretty good opportunity to repeat that and just take my time and repeat it in a controlled manner.”

In the automotive industry, Tom had learned the discipline of operating $20B plus companies on lean margins and balancing cash and expenses.

With this startup, the three co-founders saw that by just putting in $7,000 of their own money each, they could afford everything they needed and get out there doing product demos. 

It worked out well. They even created a partnership with Hyperion Solutions, a market-leading financial software company. One that would become a bit of a love-hate relationship, as although some products complimented each other, others clashed and competed with each other. Half of the company loved them, the other half were bitter rivals. 

After moving to an exclusive relationship, UpStream was able to tap into the big salesforce and customer base of Hyperion. It was only a matter of time before Hyperion would acquire them for a reported $50M. In turn, Oracle bought Hyperion. A pretty great exit given they hadn’t brought in other investors to fund the venture.

OneStream Software

Taking the lessons from his previous experience Tom saw this big need to consolidate all these products in the financial analytics space and simplify things. 

This time around they brought in co-founder Bob Powers and set out to work on what they were passionate about, and to grow with their big publicly-traded customers as they began to embrace moving their financials to the cloud and SaaS solutions.

Still harnessing that scrappy bootstrapping entrepreneurial mindset, they started OneStream Software by self-funding this new venture too. They took their time building for nine years before raising money. When they did, they did it big, and in 2019 raised a $600M funding round. 

Storytelling is everything which is something that Tom was able to master. Being able to capture the essence of what you are doing in 15 to 20 slides is the key. For a winning deck, take a look at the pitch deck template created by Silicon Valley legend, Peter Thiel (see it here) where the most critical slides are highlighted.

Remember to unlock the pitch deck template that is being used by founders around the world to raise millions below.

They were taking on the biggest companies in the world. They needed to start scaling fast to do that. They needed the best talent in the world in every department and to start really selling. 

They needed to start moving from a few hires to hiring 50 and 100 salespeople at a time. They had moved past being able to ask people to leave their comfortable salaries and stable jobs and to buy their way into the startup with the hope of making money a few years down the road. 

The waiting proved to work well. They had proven to investors that they could survive and grow at 40-60% each year, manage their money, and create value. For hires, they created a culture that proved it was reliable for them. Even through COVID-19 they hired another 100 team members in 2020. 

Tom’s Top Tips For New Entrepreneurs

  •  Keep your emotions in check and stay objective
  • Surround yourself with smart people and rely on them

Listen in to the full podcast episode to find out more, including:

  • Bootstrapping into the millions
  • Becoming the Kleenex of your industry
  • The need to break your own business every few years as you grow
  • Planning your growth in stages

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