The Startup Survival Guide: How To Make Startup Life Healthier

Founding a company is notoriously difficult. (If you’re reading this post, you probably already know this.) 

Startup life can be brutal, and even though only a fraction of founders make it big, we keep at it. Because we might change the world… if we don’t burn out first. 

Howie Diamond, the Managing Director and a General Partner of early-stage VC firm Pure Ventures, knows this firsthand. “I think for a long time, Silicon Valley has romanticized and glamorized how tedious the founder journey is,” he says. 

Howie has become passionate about supporting the well-being of founders he invests in. That’s why Pure Ventures provides access to a platform called Pilea (pronounced pill-ay) as a flagship benefit for founders. It’s safe to say Pilea is the firm’s secret sauce. 

On an episode of How I Raised It, Howie talks about why self-care is a must, how he built two funds from scratch and his favorite talking point when chatting up potential partners in his fund. 

Redefining ‘tech support’ 

Howie says those of us in the tech space have “overlooked the clear fact that founders are struggling.” 

Most founders won’t talk about their struggles because they have to appear to have everything under control and feel they can’t show any signs of weakness.

Pure Ventures, the second fund he has co-founded and managed, is “predicated on the idea that behind every great company are great people — and people are the cornerstone of any great business.” 

“Somehow in Silicon Valley and elsewhere, we sort of forgot about that,” he adds. “There are a lot of platforms that help companies grow. We saw an opportunity to build a platform to help the people behind the companies grow — across various emotional mental and physical health domains.”

Pure Ventures uses Pilea to connect its slate of startup founders with wellness and personal development services like executive coaching, sleep support, peer groups, team coaching, therapy, nutritionists and culture building. 

“Every founder wants these services, but we're investing in pre-series A companies and they can't justify the cost of them,” Howie says. 

So for one year, Pure Ventures picks up the tab for its founders to work with Pilea’s vetted professionals, who specialize in “one-to-one, high-touch” services — including nutritionists, physical trainers, holistic health coaches, psychologists and even a Marie Kondo-style “decluttering coach.” It’s both a lifeline for founders and an “insurance policy” to ensure the people they’re investing in “are getting everything they need to flourish.”

A distress call leads to a startup origin story 

Howie began his career in music management, training at CAA and repping his own band, Low vs. Diamond, all the way to a contract with Epic Records and guest appearances on late-night TV. 

He pivoted to tech startups in the early 2010s, working in marketing and business development before launching his first venture capital fund, Ranch Ventures, in 2015. He started small — amassing just $2 million from about a dozen LPs. But finding them took at least 100 meetings, says Howie. 

Let that sink in. 100 meetings and at least 88 of them resulted in a “no.” So that’s Howie’s first piece of advice — keep at it, and do it with gusto. That paid off for Ranch Ventures, which went on to fund (and continues to fund) companies like Imperfect Foods, Albert and Quip.

Even though $2 million “is obviously nothing in the grand scheme of things and in the venture asset class,” it still was a lot of money for a rookie VC. And it began to weigh on Howie. 

“I had people who believed in me and now I had to deliver results for them, so I was working overtime,” Howie recalls. “I was flying to Europe for my portfolio companies to help negotiate distribution deals. I was going above and beyond to really outperform this fund.” 

One day on a flight back from Paris, Howie hit a breaking point. Just before takeoff, one of his

anchor investors pulled out. “I had already started making investments, I'd already paid for legal,” Howie explains. “It was just a huge blow that I wasn't ready for … and on the plane ride, I had a small panic attack.”

Howie, who had never before experienced that kind of acute anxiety, explains it this way: “Basically, my engine was going into overdrive and just conked out. I had no idea what to do, who to turn to.”

The only person he could think of was iconic investor and Techstars co-founder Brad Feld, who has written about his own mental health struggles. Howie cold-emailed Feld in a “Hail Mary” effort to find help. 

In an act that redefined “angel investor,” Feld responded to Howie’s plea within 24 hours and connected him with Jerry Colonna, the co-founder of Reboot.io, a coaching platform similar to Pilea. And Colonna introduced Howie to a Bay Area coach who offered discounted rates. 

“Still to this day I have deep gratitude for him,” Howie says of Feld. 

Howie got the help he needed, but his crisis revealed a real need in the market. He realized mental health services weren’t accessible or affordable to many founders. 

“If I'm struggling, all my founders have to be struggling even more,” says Howie. 

That was the genesis of Pilea.

Me-time is money  

There was much more of a stigma around mental health care when Howie launched Ranch Ventures, but he knew that startup founders needed support to do their best work. A few years later, Howie partnered with fellow VC Jake Chapman to create a new firm, Alpha Bridge Ventures, with the thesis that “healthy founders equal healthy returns.” 

Pilea began as “Atlas,” Alpha Bridge’s in-house support services platform, but Howie and his partner quickly spun it out as a separate organization “because there was so much inbound interest from other venture funds and other companies that weren't in our portfolio,” Howie explains. 

The Alpha Bridge team connected with a professional psychologist, Kari Sulenes, who joined on to help build Atlas into a one-of-a-kind integrated leadership and human development program. They rebranded as Pilea — a reference to Pilea peperomioides, popularly known as the Chinese Money Plant and the Pass It On Plant. (Pilea plants’ large, circular leaves look like coins and grow quickly, sprouting numerous offshoots that can be propagated into more plants.) 

“This sense of magnanimity and value is exactly what we aspire to create for our clients and within our communities,” writes leadership coach and Pilea CEO Matt Thieleman on the company’s site.

Meanwhile, the investment firm rebranded as well, and Pure Ventures was born. Today, its portfolio includes functional beverage company MUD\WTR, June Shine hard kombucha and electric scooter brand Unagi.

Peace of mind and inner peace, too 

Collectively, Howie and Jake have been in Silicon Valley for over 20 years with a significant network to match. But sometimes, they get referrals that lead to top deals “because other investors want us on the cap table,” he says. “Because we have services that can be really helpful to the founders, but also to the investors’ peace of mind … We know that they know that [founders] are getting the requisite services that they need and support that they need to flourish.”

He reports that Pure Ventures has literally won deals because founders went to bat for them with other VCs, telling them how much they need Pilea’s affordable, high-quality, founder-centric services. Pilea is available to other VC firms and individual founders who don’t work with Pure, so one can imagine its impact will eventually go viral in the tech sector. 

Finding LPs is a bit more tricky. Howie tells me it’s a family affair.

“If you can get into a family office network, that's huge,” he says, noting that FOMO is alive and kicking among high-net-worth individuals, who often create their own dedicated investment management firms — “family offices” — that oversee their portfolios and find new ways to build wealth. “If you get one family office that invests in you, then the other family offices will hear about it and have FOMO and want to get in as well.”

So how can we hook up with these offices? 

“No platform or marketplace exists. It's just [about] finding entry points into these very elusive worlds and somehow making yourself known,” Howie notes, adding that email is the preferred (and often, only) communication channel for most family offices. 

Do or do not… and try, try again

“I learned a lot by doing,” says Howie, who eschewed an MBA in favor of learning on the job — first, from the agents at CAA and then by launching several of his own businesses. 

Pitching potential LPs is, like fundraising, often “literally selling” — your business, your team, your product or service and of course, yourself. But high-net-worth individuals and family offices are a particular class of investor for whom partnering with a VC fund can be an extraordinary opportunity. 

“You are providing access to a really exciting asset class and an exciting world,” Howie points out. “And investors who typically invest in bonds and low-risk stuff … or, like, real estate, this is the most exciting asset class. Because you're investing in the future, you're investing in really exciting new innovations. LPs want to be a part of the next big thing. They want to talk about it at dinner; they want to feel like they have some agency and ownership in cool stuff that's being built.”

He notes that those “boring, dull” low-risk investments return “8% or 12% at the most,” but participating in venture capital offers the opportunity to “not only deliver outsized returns but also invest in companies that are worth talking about … There’s no other asset class that can provide it.”

Although funding a fund is an attractive prospect to many investors, Howie reiterates that finding the right ones will be a lengthy process. So don’t be surprised if you find yourself taking hundreds of meetings, “because you just never know where a meeting is going to lead,” he says. 

That optimism and persistence are very much in line with Pilea’s core principles: Growing as a leader requires integrating mental, emotional, and physical health — and support is necessary to give founders “the confidence and courage necessary to succeed where others might give up.”

Raising capital isn’t for the faint of heart, but founders deserve to feel supported. I’m looking forward to watching how Pilea’s much-needed impact grows.