Sitemaps
How We Secretly Lose Control of Our Startups
Should Kids Follow in Our Founder Footsteps?
The Evolution of Entry Level Workers
Assume Everyone Will Leave in Year One
Stop Listening to Investors
Was Mortgaging My Life Worth it?
What's My Startup Worth in an Acquisition?
When Our Ambition is Our Enemy
Are Startups in a "Silent Recession"?
The 5 Types of Startup Funding
What Is Startup Funding?
Do Founders Deserve Their Profit?
Michelle Glauser on Diversity and Inclusion
The Utter STUPIDITY of "Risking it All"
Committees Are Where Progress Goes to Die
More Money (Really Means) More Problems
Why Most Founders Don't Get Rich
Investors will be Obsolete
Why is a Founder so Hard to Replace?
We Can't Grow by Saying "No"
Do People Really Want Me to Succeed?
Is the Problem the Player or the Coach?
Will Investors Bail Me Out?
The Value of Actually Getting Paid
Why do Founders Suck at Asking for Help?
Wait a Minute before Giving Away Equity
You Only Think You Work Hard
SMALL is the New Big — Embracing Efficiency in the Age of AI
The 9 Best Growth Agencies for Startups
This is BOOTSTRAPPED — 3 Strategies to Build Your Startup Without Funding
Never Share Your Net Worth
A Steady Hand in the Middle of the Storm
Risk it All vs Steady Paycheck
How About a Startup that Just Makes Money?
How to Recruit a Rockstar Advisor
Why Having Zero Experience is a Huge Asset
My Competitor Got Funded — Am I Screwed?
The Hidden Treasure of Failed Startups
If It Makes Money, It Makes Sense
Why do VCs Keep Giving Failed Founders Money?
$10K Per Month isn't Just Revenue — It's Life Support
The Ridiculous Spectrum of Investor Feedback
Startup CEOs Aren't Really CEOs
Series A, B, C, D, and E Funding: How It Works
Best Pitch Decks Ever: The Most Successful Fundraising Pitches You Need to Know
When to Raise Funds
Why Aren't Investors Responding to Me?
Should I Regret Not Raising Capital?
Unemployment Cases — Why I LOOOOOVE To Win Them So Much.
How Much to Pay Yourself
Heat-Seeking Missile: WePay’s Journey to Product-Market Fit — Interview with Rich Aberman, Co-Founder of Wepay
The R&D technique for startups: Rip off & Duplicate
Why Some Startups Win.
Chapter #1: First Steps To Validate Your Business Idea
Product Users, Not Ideas, Will Determine Your Startup’s Fate
Drop Your Free Tier
Your Advisors Are Probably Wrong
Growth Isn't Always Good
How to Shut Down Gracefully
How Does My Startup Get Acquired?
Can Entrepreneurship Be Taught?
How to Pick the Wrong Co-Founder
Staying Small While Going Big
Investors are NOT on Our Side of the Table
Who am I Really Competing Against?
Why Can't Founders Replace Themselves?
Actually, We Have Plenty of Time
Quitting vs Letting Go
How Startups Actually Get Bought
What if I'm Building the Wrong Product?
Are Founders Driven by Fear or Greed?
Why I'm Either Working or Feeling Guilty
Startup Financial Assumptions
Why Every Kid Should be a Startup Founder
We Only Have to be Right Once
If a Startup Sinks, Founders Go Down With it
Founder Success: We Need a Strict Definition of Personal Success
Is Quiet Quitting a Problem at Startup Companies?
Founder Exits are Hard Work and Good Fortune, Not "Good Luck"
Finalizing Startup Projections
All Founders are Beloved In Good Times
Our Startup Culture of Entitlement
The Bullshit Case for Raising Capital
How do We Manage Our Founder Flaws?
What If my plan for retirement is "never retire"?
Startup Failure is just One Chapter in Founder Life
6 Similarities between Startup Founders and Pro Athletes
All Founders Make Bad Decisions — and That's OK
Startup Board Negotiations: How do I tell the board I need a new deal?
Founder Sacrifice — At What Point Have I Gone Too Far?
Youth Entrepreneurship: Can Middle Schoolers be Founders?
Living the Founder Legend Isn't so Fun
Why Do VC Funded Startups Love "Fake Growth?"
How Should I Share My Wealth with Family?
How Many Deaths Can a Startup Survive?
This is Probably Your Last Success
Why Do We Still Have Full-Time Employees?
The Case Against Full Transparency
Should I Feel Guilty for Failing?
Always Take Money off the Table

Leaning In

Emma McGowan

Leaning In

Michel Feaster is not a woman you’d expect to be scared of anything. Her company, Usermind, is taking on the massive market of customer relationship management (CRM) software by providing a truly personalized customer service experience. Their focus? Millennials.

“Millennials have zero tolerance for companies that are not personalized,” Michel tells Startups.co. “Pretty much every business is facing this world where they’re going to win these hearts and ears — or someone else is going to win the Millennials.”

But Usermind isn’t Michel’s first time on the startup merry-go-round. Her first foray into the startup world was as employee #19 at Apptio. She joined Apptio with the  goal of learning firsthand the ins and outs of building a company from the ground up from serial CEO Sunny Gupta.

“It was like going to a hands-on college,” Michel says. “It was basically an advanced class in the thing I wanted to go do.”

Michel took the lessons she learned from Gupta and Apptio and set out to figure out her next step. She took three months and met “everybody and anybody,” from the entire Andreesen portfolio, to two engineers and a dog working out of a garage. Initially she thought she’d join another startup, but she realized fairly quickly that wasn’t the right move.

“I don’t know how many people I talked to, but I came away and said, ‘There’s really only one or two CEOs I’d want to work for,” Michel says. “Why wouldn’t I want to work for the other 98, or whatever that number was? The answer was that I probably shouldn’t be working for anybody anymore. I was really ready to do my own thing.”

But then Michel ran up against the one thing that comes for us all, no matter how successful or badass we are: Fear.

Fear: “Being afraid is not a good enough reason.”

Fear. It’s what holds us back from taking that leap, marrying that person, founding that company. It’s a powerful adaptive behavior that has been essential for the survival of the human race. Fear protects us from predators, from natural disasters — and from ourselves. But, according to Michel, “just being afraid isn’t a good enough reason” not to start a company.

“I kind of feel like my whole life has been a struggle with fear,” Michel says. “And the best decisions of my life are the ones I made when I was afraid.”

Michel took that fear of founding her own company and did the one thing that psychologists and behavioral therapists always recommend: She took action. In order to figure out what her company was going to be, Michel came up with around 10 questions and interviewed “a couple hundred people” who owned tech in sales and marketing. Through that process, she realized that millennials had a different idea of what customer service should be, when compared with previous generations. She saw a huge gap in the existing landscape and figured this was a chance of her to really make an impact.

I kind of feel like my whole life has been a struggle with fear. And the best decisions of my life are the ones I made when I was afraid.

“Any moment you’re terrified, probably you’re facing a growth opportunity,” Michel says. “Every time I’ve said ‘I’m afraid’ and I’ve leaned into my fear and done it, I look back and so much growth came from it.”

Michel’s leap straight into that fear was validated when she showed people her prototype of what would eventually be Usermind.

“We built this little prototype and brought it back to a bunch of people — and the reaction was amazing,” Michel says. “People were jumping out of their chair, running to the front of the room, pointing to the screen. And I thought, ‘Okay. Not only could this be big but our directional idea of how we’re solving this seems like it’s resonating with people.’”

Michel Feaster, Co-Founder and CEO of Usermind, talks during team stand-up meeting

Imposter Syndrome: “Oh yeah. Are you f*cking kidding me?”

Who hasn’t been knee-deep in a new business or project and thought, “I’m a total fraud”? That feeling is called “imposter syndrome” and it’s something that so many creative, successful people — from famous actors to world-renowned doctors to startup founders — experience at some point in their lives. When I asked Michel if she struggled with imposter syndrome as she founded Usermind, she said, “Oh yeah. Are you f*cking kidding me?”

“I don’t think I’ve become a good CEO yet,” she elaborated. “But I think I’ve become a CEO.”

And while Michel knows that imposter syndrome is pretty standard for startup founders, she also knows that gender plays a role in the male-dominated world she lives in. Scratch that — the male-dominated world we all live in.

I don’t think I’ve become a good CEO yet. But I think I’ve become a CEO.

“Men are told they should be confident since they were kids,” she says. “There are so many examples of men being told they should be confident, while women are told to be quiet, and pretty, and nice. There’s something culturally there.”

However, she also points out that a lot of Silicon Valley culture is about posturing — which only exacerbates imposter syndrome — and that has a detrimental effect on people of all genders.

“There’s this weird culture where if you say anything isn’t perfect, you might not work for me or you might not give me money or buy my product,” Michel says. “I think there are probably a lot of male founders in the valley who are feeling shitty inside. That’s why we see all these suicides. Why are founders killing themselves? Probably because they can’t really be open about the truth of what’s happening.”

Gender: “Gender bias absolutely exists, regardless of my personal successes”

You can’t escape a conversation about gender when you’re a woman leading a tech company. Especially now, with  companies like Uber and Google making news because they’re paying for prioritize gender balance early on, a woman running an enterprise company gets attention.

“I don’t think it’s a surprise that there are more women founders in the retail sector,” Michel says. “But I think it’s more of a stretch to be a founding woman in enterprise. In enterprise, it’s a macho culture. It’s a war culture.”

And, Michel says, she has a “love/hate relationship with the woman founder thing.”

“There’s definitely a part of me that bristles at the idea that what I do is meaningful because I’m a woman,” she says. “But gender bias absolutely exists, regardless of my personal successes, so I think I’ve become more passionate about advocating for women.”

Usermind company photo

In addition to her gender, Michel knows that her gender presentation also affects how she moves through the tech world. But while being a woman might make some things more difficult, she suspects that presenting as more “butch” may actually help.

“Being a lesbian, I think it’s probably easier for me to have male mentors,” Michel says. “On the one hand, I think it’s been good for me because I’m not a threat to anyone’s wife or partner. You only have to look at me to know that I’m not straight. It’s not a complicated question.”

And those male mentors have opened a lot of doors for Michel. Ben Horowitz, of Andreessen Horowitz, is a close personal friend and essential mentor who has helped her immensely. Michel clearly values her relationships with mentors, but acknowledges that “the higher you go, that’s 99 percent men.” That could, she says, cause issues for straight or bisexual women who are trying to rise in their industry.

In enterprise, it’s a macho culture. It’s a war culture.

“That’s part of the dynamic of men and women in the workplace,” says. “There’s a lot of sexual aspects that we don’t want to acknowledge.”

The answer? More women in leadership positions. While she acknowledges that there are no “easy answers” or silver bullets, Michel wants to see more companies led by women — and more exits by women founders. Only then, in her perspective, will gender be less of an issue in the tech world.

“The bottom line is, we need more leadership diversity,” Michel says.

At Usermind, Michel is doing her part to make sure that people see a strong woman founder and CEO — and an excellent product.

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