Leadership   //   February 24, 2022  ■  4 min read

‘Being a leader can be isolating’: Why mentor matchmaking is proving critical for next-gen startup CEOs

Estimated reading time: 4 minutes

Legendary Google leader Eric Schmidt calls it the best advice he ever received — get a coach.

He’s not the only one taking the advice to heart. Today, demand for CEO coaching and mentoring is rising, partly triggered by a swell in entrepreneurship and a coinciding demand for expertise and guidance from seasoned leaders.

The Great Resignation sparked a dramatic increase in workers quitting their jobs to go into business for themselves. Last year, 5.4 million applications to form new businesses were made — setting a new record — according to the U.S. Census Bureau.

SCORE, a network for small business mentors, which partners with the U.S. Small Business Administration to help small businesses get off the ground, claimed more than 730,000 people used its services between April 2020 and May 2021.

Meanwhile, management consultancy Gallup claims coaching is a billion-dollar industry with more than 11,000 certified coaches out there.

But finding the right mentor with the best experience isn’t always straightforward for those without existing personal connections. Plus, the restrictions and enforced remote working caused by coronavirus have made many feel isolated and blocked a lot of the in-person connections an entrepreneur could typically have made in networking situations.

Online marketplaces that connect startups with experienced mentors have cropped up to fill that void. Bolster is one of them. The online marketplace, launched in September 2020, links startups with external executives seeking mentoring or coaching gigs, as well as full or part-time projects.

Bolster CEO Matt Blumberg said the matchmaking helps companies scale their executive teams and boards, and gives them access to talent that can be transformative to their businesses. In other words, people with “been there, done that” experience, he added.

Last week, Bolster unveiled two additional options: Prime, an 18-month mentoring program; and Ventures, an early-stage venture fund.

Alex Tepper is a Prime mentor. “Founders have an often unquenchable passion to build the company of their dreams,” said Tepper, “but that doesn’t necessarily mean that they have developed all the skills to do so.” Tepper has experience with American Express, GE Ventures and Techstars where he held a variety of executive roles.

“Mentors help provide strategic and tactical advice to startup founders, augmenting the skills and knowledge in areas where the founders need help and/or an outside perspective,” he added.

Kelsey Recht is also a Bolster Prime mentor. She was CEO and founder of booking platform VenueBook. Recht believes keeping having distance from a startup’s daily operations is beneficial. “Often things can be more clear when discussed with someone who is not as close to the day-to-day but understands the business intimately,” she said.

Bolster Ventures program is a $6 million early-stage venture fund that will invest in up to 60 Prime clients, cutting $100,000 checks on average to each entrepreneur.

“When you ask any startup CEO what major constraints exist for them in starting businesses, you often hear two major themes: [a]ccess to talent and access to capital,” said Bolster’s CEO Blumberg.

That said, getting that access isn’t cheap. Clients who sign on for Bolster Prime membership are facing fees that start at $37,500 for the 18-month mentorship.

The online marketplace has its own schedule of charges that are less expensive.

“We believe the investment we are making in our relationships with Bolster mentors will accrue exponentially as our business evolves and matures,” said Shane Kiernan, CEO of Iamus — an artificial intelligence and robotics company, headquartered in Dublin, Ireland.

“Startups may be lean and mean and very often they are chaotic which is fine for the earliest days. However, for a startup to succeed in the long term, regardless of a pandemic, they need to invest in the building blocks that lead to success,” added Kiernan. “This is where mentorship is so important as mentors have typically been through the rodeo before and imbue their experience, insights, and network to help a startup go through the evolution process that leads to success.”

Startups founders have found having a platform that links them to the right expertise, has proved invaluable, particularly over the last year. “Being a leader and especially a CEO can be very isolating — even more so during the current situation with the pandemic and 100% remote work,” said Sherisse Hawkins, founder and CEO of Pagedip, a document authoring tool based in Boulder, Colorado.

One of the markers of a good coach or mentor is one who encourages self-sufficiency, so that when business conditions change — as they have over the past two years — startup founders can adapt and evolve with those changes.

“The value of a mentor increases over time and that is part of what makes the Bolster program so unique,” said Hawkins. “It is an agreement to consistently and deliberately meet to discuss success and challenges, opportunities and risks with an unbiased expert.”

Bolster’s CEO says it’s too early to label the Prime program a winner. “As any VC [venture capitalist] will tell you, success is a long-term road for venture-backed businesses. What we hope to see over time is that startups we work with are quicker to market, more adaptable to business pivots, and accelerate through the growth stages of their business with a straighter line than might be typical of a first-time startup CEO,” he said.