Founder Guidance

Karen Wickre

It takes a tremendous amount of courage to leave the comforts of corporate life and start your own venture. There’s a lot you’re going to learn as you go. But Karen Wickre has practically written the playbook on how to do it. Spoiler alert: She’s crushing it.—Jamila Huxtable, Founder Brew reporter

Karen Wickre, a communications professional whose career includes years at companies like Ziff Davis, Google, and Twitter, left her last full-time role in 2016 with a trade-off she understood clearly: more freedom, and fewer years of earning a steady corporate salary.

In the decade since, she’s built a consulting career that doesn’t follow a predictable arc. Some years are busy, others depend on quick projects or retainer work that comes and goes. Wickre describes it as an “undulating income curve”—a rhythm that only becomes clear late in the year.

Wickre spoke with Founder Brew about the lessons she’s learned after moving from full-time employment into solo consulting, and the first step she advises for anyone blazing an independent path.

What’s one mistake you see first-time founders or early consultants make over and over because they lack experience?

It’s the whole setting up of it where people research: “Do I need an LLC?” or “Do I have to incorporate?” and spend a lot of time on their brand and their domain names. I understand why you want to make a mark and establish yourself, but you don’t have to do all of those things at the very beginning—and you may never have to do some of those things.

As a sole proprietor, you can have a separate business credit card if you like, but you can report based on your Social Security number and have business expenses. You don’t have to pay for incorporation…It makes things cleaner, but it’s also not hard to say: “This is what I do all the time, and this is my business, and I’m a sole proprietor.”

Read more about Karen Wickre’s experience as a sole proprietor.—JH

      

Sponsored By Awesome CX

The company JAANUU was built on the idea of rethinking medical apparel. As the company scaled, founder Mike Alexander faced a hard question that most startups run into: How can you protect your product as your brand grows?

Alexander sat down with Scale-Up Stories from Awesome CX to discuss the approach he took. In the Product Scaling Playbook, he explains how he applied his original vision to the company’s next growth stage.

Take a look at the playbook to learn five plays from JAANUU’s scaling journey. Here’s a peak at what they cover:

• protecting your core differentiator
• looking beyond competitors for inspiration
• defending quality under pressure
• building a product-obsessed culture

Get ready for a hefty dose of knowledge, insights, and inspiration. Grab your copy of the Product Scaling Playbook.

Starting Your Business

Sabeen Khan

Sabeen Khan’s misstep wasn’t fatal, but the sinking feeling of messing up something important for your company is relatable for any founder. It’s not easy to admit to a mistake, but everyone can learn from it.—Dan Latu, Founder Brew senior reporter

In early 2024, Sabeen Khan filed what she thought was all the right paperwork to start Khoobi, her dream beauty and wellness app.

She originally chose to file her business as a limited liability company, or LLC, “because it came as a package deal with a website and I was like, ‘This is what official businesses do,’” she explained. “When you look up or Google ‘How to start a business,’ it’s always like ‘Start an LLC.’”

The former Wall Street analyst had already quit her job and moved in with her parents to focus on building Khoobi, which she described as a “prediction intelligence platform for beauty brands.” She hired a founder coach and set up the first call a few weeks after officially filing.

During that first meeting, the coach told Khan that some of her choices could prevent her from successfully raising venture capital funding. Specifically, one of the mistakes, the coach said, was that Khan registered her company as an LLC and not a corporation, or a C Corp.

After the call, Khan closed her laptop and cried on the phone to her friend.

“I think I needed the tough love,” Khan told Founder Brew.

Read more about how Sabeen Khan realized—and fixed—her mistake.—DL

      

Founder Leadership

Judy Thelen and Eliot Frost

The co-founders of social restaurant review app Beli worked together, went to business school together, and married each other—now that’s what I call commitment! Judy Thelen and Eliot Frost trust each other more than anyone and have learned a lot about where to include, and omit, partners and friends in a successful startup journey.—Ava Manson, Founder Brew associate booking producer

Judy Thelen and Eliot Frost built their relationship around the same activity that inspired their company: dining out.

The married couple, co-founders of social restaurant review app Beli, met while working at McKinsey in New York. The self-proclaimed “restaurant-obsessed” pair created a Google map that tracked everywhere they ate together. “It was ranked, color coded, notes, favorite dishes, all that,” said Frost.

Together, Thelen and Frost attended Harvard Business School, and their dedication to tracking restaurant data became more than a hobby. The two launched Beli in the 2021 and have since collected over 120 million restaurant ratings—largely from Gen Z and millennial users—according to Thelen.

In a conversation with Founder Brew, Thelen and Frost discuss launching their consumer app and the best rules to follow when married to your co-founder.

What would you tell someone thinking of founding a company with their partner?

Judy Thelen: For us, it’s our biggest superpower. The fact that I can work with someone that I completely trust makes making decisions a lot easier, and we can be very honest.

If you’re founding with a partner—just as you’re picking a co-founder in general—picking someone who has a complementary skill set is really helpful.

Read more about how Beli’s co-founders balance business and life.—AM

      

Sponsored By Awesome CX

Protect ya product. Wondering how you can build a product-obsessed culture and maintain your core differentiator as you scale? JAANUU CEO Mike Alexander answers those questions and more in the Product Scaling Playbook from Awesome CX. He offers up five plays from JAANUU’s scaling journey that you can apply to your business. Give it a look.

Founder Leadership

Angie Hicks

Speaking with Angie Hicks was a delight, and eye-opening. She believes strongly that founders need to surround themselves with the right people, and that the culture of a company is its strongest asset—two ideas that, to me, turn the thought of a successful business from numbers on a spreadsheet to something far more meaningful.—Megan McCarthy, Founder Brew editor

Angie Hicks didn’t set out to become a name-brand entrepreneur.

In 1995, she was a recent DePauw University graduate with an economics degree and a job offer from her boss at a former internship, Bill Oesterle: to help him create a resource for homeowners in Columbus, Ohio, to find local contractors.

“I knew nothing about starting a business,” Hicks told Founder Brew.

The company is now known as Angi, keeping the most distinctive part of its identity. It also kept Hicks, who today serves as chief customer officer and continues to be the face—and name—of the company.

In conversation with Founder Brew, Hicks spoke about her 30-year entrepreneurial journey, and why best businesses are built from the right people.

“I would take an A team with a B idea over a B team with an A idea anytime,” she said.

What advice would you give to founders who are at that crossroads trying to find the right people to bring on, trying to settle on the idea that they’re so passionate about?

It really starts with you and an assessment of what you’re good at and what you’re not. You have to be super honest. A lot of times founders want to say they’re really great at everything. They’re not.

You need to make sure that you can bring people in that can complement you. Like, me? I wasn’t the salesperson. I knew we were absolutely going to have to have people that had that skill, that could bring that skill to the table.

It’s your baby, and it’s hard to let people do the things that they need to do. Delegation becomes hard. How are you giving them that space? Because if you can’t be honest about what you need and give them the space to be successful, it’s never going to work. I would encourage them to do some soul-searching and figure out what that is.

Culture actually makes or breaks the company. A CEO or a founder who says they don’t have time to dedicate to building the culture will have a bad culture, and that bad culture will take care of the company for you. This is not about building a culture deck. This is not about bells and whistles. This is about: How do you walk the walk and talk the talk everyday? So, what things are you doing?

Read why Angie HIcks thinks the most important part of a company is the people involved.—MM

      

Stat: 1993. That’s the year state-based Self-Employment Assistance Programs were first authorized by the federal government when that year’s NAFTA bill was signed into law. These programs allow eligible unemployed workers in select states to collect benefits similar to unemployment while working on their own businesses. (Founder Brew)

Quote: “This is why you don’t let family operate on family, right?”—Fourplay co-founder Julie Griggs, on how painful it was for her and co-founder Danielle Dietzek to finally wind down their dating app startup (Founder Brew)

Read: What is it like to go from taking orders to giving them? We spoke with several founders with a military background on how their time in the US Army, Air Force, and Marines shaped how they run their companies. (Founder Brew)

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