Susan Hunt Stevens says she's probably had every form of funding for WeSpire that could be had for a business — angel investors, seed funds, debt, strategics, private equity, some venture funds, family offices, etc.

The company's founder and CEO says that was a deliberate decision because she couldn't figure out how big the market was back when she founded the employee engagement software and campaign company in 2010 and went out to raise capital.

"There just was no data," she says. "And one of the things I learned from my first startup is that if it's not a clear giant market with a giant opportunity, certain funding just doesn't match."

That led Stevens to bootstrap for the first year and a half before raising capital from seed investors. From there the company was able to start attracting small funds from individuals and a family office.

Today, the company has not only raised a large round of capital — a $13 million Series B round in August 2021 — but the company has also brought expertise in for scaling and building a sales and marketing engine around the company's product.

When a company lands a round of that size, the focus is often on the amount. But the other important factor are the investor who are able to lend their network and expertise to the venture.

"That was the part that I was most excited about with this round," she says. "There's a lot of money out there right now and so who you get money from is actually almost more important. Are they going to be helpful to the company? What's their attitude towards founders and founding teams and how they support?"

Certain investors want to bring in their own people. For a founder who's ready to move on, that could be a great fit. But those who have a team and really want to make that run, they've got to make sure they have investor alignment with not only the strategy for utilizing the capital but the support that the company needs and what it’s trying to accomplish.

Fundraising, Stevens says, is exhausting.

"An investor's job is essentially to say no," she says. "They say no 95 percent of the time. They might do six deals a year, 10 deals a year at the most, and they're going to meet with hundreds of companies. And if you go into every meeting feeling like you've failed if they say no, you're not going to be able to be successful."

Stevens says her approach has been to go into every meeting and determine what she can learn from the meeting — about the investors, whether they're a good match for the business, and, maybe most importantly, what feedback they give on the business.

"If you're a good pattern matcher as a founder/CEO, the fundraising process is actually when you really start to see the patterns emerge for what people are concerned about," Stevens says. "And if a bunch of people are concerned about it who invest professionally, there's probably a problem there that you need to go fix."

Stevens spoke at the Boston Smart Business Dealmakers Conference about her experience raising capital. Hit play on the video above to catch the full interview.