The lightning-fast Series A (that was 3 years in the making)

Christine Tao runs Sounding Board, a business founded in 2016 that offers executive coaching services to leaders at major companies like Kraft and Heinz. But not long ago, she was the one in need of a coach.

But prior to that, Tao found herself in a new high-powered position at the mobile advertising company Tapjoy. Although she had plenty of sales experience, she was now working in an executive role leading the company’s entire sales staff. It was a tough learning curve. But the company’s board paired her with an executive coach, Lori Mazan, who ultimately helped Tao succeed.

“That really had a profound impact, not just on my professional development, but my personal development as well,” Tao said.

Later on, Tao and Mazan teamed up to launch Sounding Board, a service with a proprietary algorithm that matches participants with coaches. Its capabilities-driven model can even measure the impact of the coaching.

At the beginning, Tao didn’t have many resources. Ultimately, she raised $15 million in a pre-seed and Series A round. An impressive group of investors got in on the action, including Roy Bahat of Bloomberg Beta, Charles Hudson of Precursor Ventures and Maha Ibrahim of Canaan.

On an episode of the “How I Raised It” podcast, Tao talked about raising money quickly, honing your strategy and getting back on your feet after all you hear is “no.”

Start out scrappy

From the very beginning, Tao had big ideas.

She wanted to make coaching accessible to all sorts of executive leaders. The service wouldn’t just be for correcting bad behavior, as coaching had been in the past, but about helping executives grow and develop so that they could lead their businesses with their best foot forward. Tao also aimed to make coaching available through remote technology.

The problem was, Tao didn’t quite have the resources to get started. Initially, turning those ideas into a functioning business seemed about as realistic as climbing Mount Everest.

But Tao was determined, crafty and up to the challenge, happy to use the few resources at her disposal. First, she asked her sister, a UX/UI designer, to make a prototype app. Tao shared the prototype with everyone she knew in her LinkedIn network, just to get feedback. Mazan also used her connections in the industry to sign up Sounding Board’s first few coaches.

On the financing side, Tao began her company by bootstrapping before raising a penny — all while pregnant with her son.

Leave your ego behind and ask again

When the fundraising finally began, Tao didn’t immediately bring in the dollars she’d hoped. In fact, in her first attempt at fundraising, the answer across the board was a resounding no.

“I’ll share something which is not always shared: Almost all of the investors that we brought on at Sounding Board actually said no the first time I pitched them,” Tao said.

The crux of the matter was simple enough: Tao had done some piloting, but she hadn’t yet built out the tech. She was still looking for a technical co-founder, too. In other words, she had an idea, but nothing tangible.

It wasn’t long before Tao’s fortunes turned.

After unsuccessfully pitching Bahat at Bloomberg Beta in 2016, he was leading her pre-seed round a year later.

She later asked him, “What made you decide to … pull the trigger this time? I’m pitching you the same idea.” His response, according to Tao: “You basically accomplished everything you told me you were going to do and more.”

In short, Tao said to show investors that you’re committed to following through. That makes all the difference.

Set up a pitch “war room”

Tao finished her Series A round in six weeks, largely because she took an intentionally strategic approach to fundraising.

Before pitching, the team dove deep into their long-term strategy, thinking about how their founding story could work as a compelling narrative. They also considered market opportunities; although it’s impossible to control the market, Tao said, you can still explain to investors why your particular product or service fits into the market as it exists now.

Tao and her team also reconsidered their strategy after every “no” and every piece of feedback.

“It was like a war room after meetings. We’re calibrating feedback; we are thinking about which answers we didn’t feel like we had answered strongly,” Tao said. “We come up with decks and slides to really paint that picture so that we could go into the next meeting saying, ‘OK, if we think somebody’s thinking about this, let’s get ahead of that and actually talk about that now.’”

Thanks to this strategy, Tao and her team met with Ibrahim of Canaan early in the process of her Series A round. Ibrahim ended up leading the round, and Tao only hosted about 10 to 15 investor meetings in total before raising $13.1 million.

Steer the conversation

Strategy can also help you “run your process with confidence,” Tao said.

It’s important to be confident when pitching to investors, and it can help to think of them as equals. Tao considered each investor to have a treasure trove of unique information that she could leverage for Sounding Board. These various areas of expertise also helped Tao initially connect with investors at fundraising meetings.

“Each investor themselves also has areas of expertise from their past lives as operators or their investments. … I’d find different touchpoints [and] be able to engage them around things that I was thinking about around the business,” she explained.

The more research and preparation you do, the more you can remain in control of the meeting instead of letting investors drive the conversation. And, Tao pointed out, that’s key.

“I want to make sure they understand my business, and [I want to] be able to drive the conversations in that way,” Tao said. “My advice: … Think about driving those conversations.”

Julia Collins and Sarah Kunst outline how to build a fundraising process