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Denver Startup Week sign during the 2022 event. (Tamara Chuang, The Colorado Sun)

During the opening event of Denver Startup Week, Makisha Boothe, founder of Sistahbiz Global Network, shared one thing she had in common with Ben Wright, founder of Velocity Global, which raised $400 million in its latest investment round. 

They both descended from entrepreneurs.

“My great-great-great-grandfather responded to an ad in the paper in St. Louis and became a horse trainer,” said Wright, who started the human resources technology firm in 2014 that is now in 185 countries. “They put him on a train (to Colorado) and when he got out here, he said, ‘I don’t know how to train horses.’ And they’re like, ‘Well, we got you a ticket to get here and I’ll teach you how to train horses.’ That’s how we got to Denver.”

For Boothe, whose company coaches Black women entrepreneurs on how to accelerate their business and find funding, it was her great-grandmother.

“My great-grandmother, the only Black woman on the block in Harlem, New York, who owned a brownstone and ran her business out of it, ran a micro-lending program out of her basement because Black people could not get access to banks,” she said. “And so here I am years later … helping Black women entrepreneurs grow their business.” 

Ben Wright, founder of Velocity Global, and Makisha Boothe, founder of Sistahbiz, interview one another at Denver Startup Week on Sept. 19, 2022. (Tamara Chuang, The Colorado Sun)

This year’s Denver Startup Week, touted by organizers as the nation’s largest free event of its kind, highlights startups by entrepreneurs from underrepresented groups. Even key sponsor Amazon held a session called “Alexa: How is Amazon supporting underrepresented founders?” on Tuesday. 

The opening-day crowds were smaller than in years past. Organizers are expecting about 10,000 registrants this week, or about half the number of attendees in 2019. But the shift to return to local speakers rather than bringing in an out-of-town keynote for the kickoff helped Denver Startup Week get back to its roots. Local founders talking to local founders. The kickoff featured founders of multibillion-dollar valued local “unicorns” talking with their earlier-stage counterparts, like Boothe and Wright.

One of the topics of great interest among entrepreneurs is funding. Colorado startups hit a record year for venture capital, raising $6.8 billion split unevenly among 583 companies.That was triple the amount of the last record, which was reached the prior year. Deals were just larger than in past years, including the $1.4 billion raised by Sierra Space in Louisville.

As of June 30,  Denver-area venture funding was around $3 billion, according to conference organizers. But not a lot of the funding is going to women or minority founders. 

That’s one thing Boothe pointed out in how Sistahbiz and a company like Velocity Global differ. 

She cited a data point from the “2019 State of Women-Owned Businesses” report by American Express that found Black female founders averaged revenue of $24,000 compared with $142,900 for all women-owned businesses. That doesn’t even touch on what white male founders average, she remarked.

“We want to get her past that friends and family round and help her prepare her own strategy so that she can get capital,” said Boothe, who has struggled to raise venture capital. Despite that, she’s managed to expand her coaching business to 26 states.

Lee Mayer, cofounder of high-tech interior design site Havenly, said that when she started raising funding for her company, she heard 140 “nos” before she got her first “yes.” 

“Imagine asking 140 girls or guys to prom and they all say no. Imagine applying to 140 colleges and they all say no. It was dramatically terrible. It taught me to persevere,” Mayer said. “Around the 140th no, I was thinking of giving up and going back to the (corporate) job. And if I had done that, the last five to eight years wouldn’t have happened. And I wouldn’t have gotten the 141st person, who said‘yes.”

Lee Mayer, right, founder and CEO of Havenly, meets with Cristina DeVito, CFO, inside MayerÕs office at the Zeppelin Station building in the RiNo district on April 6, 2021 in Denver, Colorado. (Kathryn Scott, Special to The Colorado Sun)

Havenly, which is still working on getting to profitability, has raised nearly $100 million. Earlier this year, it acquired furnishings brand The Inside. Mayer, herself, has become an investor in women-led startups, including in Halfdays, a Denver-based women’s ski wear apparel brand founded during the pandemic by Ariana Ferwerda and Olympian Kiley McKinnon. 

At Denver Startup Week, Mayer was chatting with Ferwerda who asked her about work-life balance. Mayer’s response: Having it all simultaneously is a myth.

“The reality is that over the course of your career or life, you can certainly have it all but sometimes in that moment, you can’t do it all,” Mayer said. “And that’s perfectly OK.” 

Chamba founders Diego Montemayor, David Ruiz and Corina Hierro are on the left, joined by their coworkers during Denver Startup Week on Sept. 19, 2022 in downtown Denver. The Chamba app helps connect workers to available restaurant jobs. But uniquely, it helps connect Spanish-speaking workers to English-speaking restaurant owners and managers in need of employees. (Tamara Chuang, The Colorado Sun)

Denver’s unicorns

  • AgentSync, an insurance compliance software that last raised $75 million, valuing the firm at $1.2 billion
  • Boom Supersonic, which is developing supersonic jets for passenger travel, has raised $247.5 million, according to Crunchbase.
  • DispatchHealth, which provides medical appointments at home, last raised $200 million, which put the company’s value at $1.7 billion.
  • Guild Education, which provides education opportunities to workers at large companies, raised $150 million last year and was valued at around $4 billion  
  • HotelEngine, which connects business travelers to hotels and lodging, last raised $65 million, putting its valuation at $1.3 billion.
  • Ibotta, developers behind the cashback shopping app, reached a $1 billion valuation back in 2019.
  • JumpCloud, a cloud-based service of IT resources, raised $159 million last year for a valuation of $2.56 billion, according to VentureBeat.
  • Melio, a payments platform for small businesses that has a big office in Denver, raised $250 million last year, which valued the company at $4 billion.
  • Quantum Metric, a cloud-based service where coworkers can build digital products, raised $200 million last year, pushing its valuation to more than $1 billion.
  • SonderMind, which matches folks in need of mental health support to therapists, added $150 million in investment last year, valuing the company at $1 billion.
  • Uplight, which makes software products focused on clean energy, was valued at $1.5 billion, according to Reuters.
  • Velocity Global, which provides a human resources software to manage workers, raised $400 million in May, pushing it to a “multi-billion dollar valuation,” said the company.

The diversity that mobile app Chamba brings to the job market has helped the Denver startup get noticed. The bilingual app provides guidance to Spanish-speaking workers to help them build a digital resume and then puts them in touch with restaurant owners and managers who need help but may not speak Spanish.

But it wouldn’t be as authentic if you didn’t have someone like Diego Montemayor and his cofounders at the top. His cofounder David Ruiz lives in Colombia (they met after Montemayor said he typed in #developer online while in Colombia and Ruiz “was the only one who wrote back.”) and Corina Hierro, a Latina and Chamba’s founding member and community manager, came from Telemundo. 

“Community is key, especially because we work with the hard-to-reach community that you’re not going to find” in the places many employers in America search, said Montemayor, who studied political science at the University of Colorado. “Focusing on that community that’s there, ready to work but hasn’t been served with technology has helped us.” 

While Dan Caruso, a cofounder of Zayo Group and Level 3 Communications (now part of CenturyLink), didn’t take the stage on Monday, he was in the audience. And afterward, he walked up and chatted with some of the younger startups. He also runs Caruso Ventures in Boulder and has invested in Chamba, as well as SonderMind, Havenly and others through Endeavor Colorado, which helps startups grow faster. 

“I am proud and humbled by how far Colorado’s scale-up ecosystem has progressed. We now have well over a dozen unicorns,” Caruso said. “Colorado’s entrepreneurial leaders are thinking bigger and achieving more than at any other point in our state’s history — and our entire community is benefiting from their innovations and accomplishments.”

Tamara Chuang writes about Colorado business and the local economy for The Colorado Sun, which she cofounded in 2018 with a mission to make sure quality local journalism is a sustainable business. Her focus on the economy during the pandemic...