From Dropshipping Side Hustle to M&A: Mark Woodbury’s Playbook for Aspiring Digital Founders

The Small-Town Start That Changed Everything

Mark Woodbury didn’t enter entrepreneurship through glossy startup lore or with Silicon Valley seed funding. Instead, his journey began on the football field at Colorado State University and in a modest Northern California town. While uncovering his drive for business, Mark realized college life wasn’t for him—but the friendships he made lit a fire. Surrounded by peers chasing self-employment—even when their side hustles fizzled out—Mark saw that building something on your own terms was actually possible.

First Hustles: From DIY Skill-Building to Self-Taught SEO

Initially, Mark kept it simple: he offered SEO and basic web development services to local businesses, picking up everything he needed to know from YouTube and online guides. By handling real client work, he built practical skills and confidence. It wasn’t fancy—just grit, Google, and late nights in his dorm room. Through these hands-on gigs, Mark began to see how digital services could be turned into real cash, even with next to no startup funds.

The Leap Into Dropshipping—and a Six-Figure Sale

Late 2013 brought a turning point: Mark discovereddropshipping. He wasn’t afraid to get his hands dirty in research—digging through Google Shopping and AdWords to spot search volume and competitor weak spots. Metalworking and woodworking equipment became his winning bet. With only personal savings and hustle, he pitched hard to suppliers for distribution rights, built a scrappy but functional eCommerce site, and started seeing orders roll in.

Despite growing profit and learning the ropes of inventory, supplier management, and customer support, Mark’s interest waned after a year. Hungry for something new, he decided to move on—but not before trying to sell his site. When finance and due diligence questions got overwhelming, Mark quickly called in a business broker. The result? A successful low six-figure exit. For a college grad with no outside backing, it felt like winning the lottery.

Identifying Broken Systems: The Upward Exits Venture

Selling his dropshipping business opened Mark’s eyes to how clunky and outdated the brokerage process was, especially for web-based businesses. Traditional brokers just didn’t get SaaS, content, or affiliate sites. With his finance background and fresh experience, Mark saw the need for smarter support—and alongside co-founder Alex Shute, launchedUpward Exits.

Upward Exits focused on digital businesses hitting $200k-$500k annually. Their pitch? Give honest support and a modern approach in a space stuck in legacy methods. They started with direct-to-consumer brands and soon moved into content, affiliate, and e-commerce sites as well. Mark’s time there was about more than process—it was about learning the psychology of founders, buyers, and broker networks—how do you actually build trust and get deals truly across the line?

The Pivot to Raincatcher: Stepping Into the Big Leagues

In early 2021, Mark’s reputation caught the attention of Raincatcher, a well-known M&A advisory firm. After connecting with Raincatcher’s leadership, he joined as the Managing Director of their Digital Division. His job? Overhauling the process for representing SaaS companies, eCommerce shops, marketing, and content businesses ready for acquisition—advising on valuation, packaging, marketing, and negotiation from start to finish. At Raincatcher, no two days are the same. One day, he’s running diligence on a rapidly scaling SaaS product. The next day, he’s training a founder how to prep documentation, or negotiating tough post-sale terms. Mark shoulders a heavy load—client trust, complex deals, managing a growing team—but calls it the most rewarding work he’s done. As he says: having the freedom, money, and a chance to work with passionate entrepreneurs is what motivates him to "tap dance to work" just like Warren Buffet.

Lessons for Aspiring Founders: No Shortcuts, Only Smart Moves

• Start Small, Think Big: Mark’s earliest wins were modest—an SEO gig here, a one-page website there. But every check built toward his end goal. You don’t have to launch an empire overnight.
• Network Like Your Life Depends On It: Key opportunities came from Mark’s tight circle—peers pushing the limits and showing a different way. Your relationships open doors algorithms can’t.
• Don’t Be the Bottleneck: When it’s time to sell or take on a job beyond your skillset, call in experts. Mark brought in brokers rather than tank a sale—don’t let pride cost you big money.
• Be Ready to Move On: Interest will fade. Don’t stick with a business just because you “should.” Mark sold when his passion waned and rolled capital into his next move.
• Learn-by-Doing: Mark didn’t wait for a class or certification—he dove into self-teaching and put knowledge to the test building real projects. The tech world rewards doers, not perfectionists.

Mark Woodbury’s Take on Success

For Mark, success isn’t just the cash or a fancy title. It’s the freedom to work with people he likes and respects—and to solve problems most advisors and brokers can’t. His drive? Continuous learning, honest feedback, and celebrating the wins of entrepreneurs he supports daily.

Raincatcher’s Digital Division now stands out for doing what old-school brokerages won’t: treating online-first businesses with the nuance and respect they’re due, helping founders get real value for their years of sweat and risk.

Final Word: Blueprint for Digital Growth

Mark’s journey—small-town origins to M&A leadership—shows what happens when someone turns every misstep, sale, and network introduction into a learning opportunity. For those aiming to make a mark in digital business, there’s no magic formula, but Mark’s playbook offers a damn good map: learn fast, adapt, and never stop moving.