Serial entrepreneur Aaron White is having a great year. In May, Profitwell, a pricing and retention platform White co-founded, was acquired for $200 million. In February, his SaaS management platform Blissfully was acquired by SaaS buying platform Vendr, where White now serves as chief technical officer. And a few months ago, the Vendr team closed a $150 million series B funding round.
White’s road to success was marked by a number of challenges and setbacks. In addition to a few failed startup attempts, White struggled to maintain his mental health and ultimately had to find a way to balance both his entrepreneurial passion and personal life.
“It feels like my whole career has been building to this in a way,” White says. “For a while I had been having crushing anxiety about failing as a man, as a partner, and as a businessman. I could not see the forest through the trees. I had to learn how to know when to keep going and how to take care of myself along the way.”
White is among the featured speakers at fnSummit 2022, Founders Network’s annual conference that brings together founders, investors, and partners in the startup ecosystem. As part of his keynote, White provided his insights on the value of business acumen for technical founders, the power of perseverance, and how to take care of yourself throughout your startup journey.
Trial and Error
One of the first entrepreneurial endeavors White was a part of was a debugging software startup team. Ultimately, that business failed because no one was buying the software. However, the experience taught White that there was more to business building than just code. So, he carried on with his startup journey and launched another tech company. That endeavor gained more traction, attracting half a million users, but ultimately failed as well.
“I thought I’d learn by doing, and I incorrectly assumed I was ready to do my own startup,” White says. “We had half a million users, but we failed at everything else. We failed at fundraising, hiring, monetization, and marketing. We failed at focusing the product. I learned a lot of hard lessons. To do a business really means understanding everything about a business from sales and revenue to marketing and people.”
More to Learn
White’s next stop on his startup journey was was an edtech company that was able to raise $14 million in just six months in 2010. Despite the merits of the technology White and his team built, the startup struggled to find product-market fit.
At this point, White took on a vice president role at a venture capital investment firm which enabled him to go back to school to get his MBA and learn more about software businesses. At the same time, he was helping to launch a software pricing services startup that would ultimately become Profitwell.
“On the VC side, I learned a ton about software broadly,” White says. “I also used this time to start gaining perspective on the rise of the SaaS ecosystem from the side of the SaaS sellers. Saas was changing everything.”
A Perfect Match
Next, White began work on Blissfully. After what he had experienced with past endeavors, White and his team were hesitant to go all in on fundraising and instead focused on their product and growing their customer base. However, this approach created challenges when Blissfully was ready to scale and expand. Ultimately, Blissfully’s partnership with Vendr proved to be the perfect solution for both startups.
“We did a few very modest rounds of venture capital. We only ever raised $7 million, but managed to get hundreds of customers. It was going good but not great,” White says. “Startups have original sins that are very hard to correct because they’re so deeply baked into your culture or approach. At Blissfully our original sin was we were capital shy, but we needed significant capital to build out a vision. When Vendr came along, we sort of solved each other’s problems.”