What Went Wrong? A Founder's Answer

"What went wrong?"

The middle-aged man sitting across from me at Starbucks at 4 p.m. on a Wednesday in August of 2022 was the CFO of an event experience company. He was interviewing me for a director-level role I could confidently do with 11% of my capacity.

He wants to know why I'm job hunting after six years of co-founding and being CEO of ArcVida, a nationwide, modern, B2C career guidance platform for professionals.

I wasn't expecting that question, so I fumbled around. But it's like asking what was wrong with a marriage after your spouse of 10 years dies in a crash. And, it stuck with me in part because when my daughter's father and I divorced in 2011, after a 10-year relationship the questions felt the same. Really, the answers felt the same - "it's complicated."

Almost a year later, I want to share some of my mindset, confidence, belief, resources, and blindspots.

Mindset

I believed I could learn whatever I needed to learn. Tools exist. The world will change. Boy -- didn't understand that a self-funded B2C tech company learning curve is a straight vertical line, and I didn't plan to become SO technical.

Confidence

I knew that I could find great people to work with to solve a pretty dumb problem. I'd had a lot of professional growth and recent entrepreneurial success. And wow - the BEST part of the journey was really understanding the incredible talent that is available in the world. Our mission of helping people land great jobs attracted kind, generous professionals with every kind of functional skill. I loved working with them and learned so much about attracting, compensating, communicating, and motivating great people.

Belief -

I was convinced that we could create incredible value for people with a service that didn't otherwise exist. And we DID create quantifiably impressive value in paychecks and jobs and qualitative value in life satisfaction. This service doesn't exist anymore.

Resources

-The obvious resources were financial. I was able to use savings, used my professional skills to get paid well for "side" consulting, and have a supportive spouse who paid rent, brought groceries, and covered us on his health insurance for longer than we both wanted. I'm also frugal - (still) drive an old car, like shopping at thrift stores, and send my kid to a public school.

-Social capital was an enormous resource. I had former colleagues, classmates, and some friends who trusted me enough to jump into a raft to row while we built a ship; dear friends who referred me to wonderful attorneys, people who referred customers, bankers, and freelancers, and vouched for me personally and professionally, as well as several incredibly supportive family members.

-Health - Throughout these years, I was (and continue to be) blessed with good health and great energy. ?

-Grit. No, really y'all. I have a lot of resilience and probably too much grit. I love the maxim that founders don't quit, they just stop pivoting. ?

BlindSpots

1. Media coverage about founders is driven by VC PR machines. Very little public information about the real tech-startup journey exists.

2. Investors enjoy funding things other investors want to fund. ?It's a pretty social outlet for many, many investors so pattern-matching matters.

- If the VC doesn't have a thesis of funding founders like you in exactly the same stage, then don't waste time asking.

-Timing matters.? See - 71% of investments in 2023 going to "AI" companies. ?In 2021, we prototyped AI with awesome data scientists and the response I got from the few investors I was able to meet with was "It doesn't seem like a technical- enough solution."

-Visible exits matter. If the industry doesn't have lucrative, recent, public exits with impressively large sale prices, good luck raising. Or don't expect to raise.

- Being a visionary founder means creating the future. The future doesn't exist yet. ?Most people won't believe you are creating the future and cannot understand this.

3. When you run out of money, you run out of time.

4. All government support is tied to a W2. ?Working for equity meant that all founders like me were not eligible for pandemic-related funding. ?Building a tech-company meant that we were ineligible for local pandemic loans or grants.

5. Professionals who will pay thousands of dollars for an undergraduate or graduate education won't pay $1000 for a career-changing service. They'll wait for many months of failing on their own to land a great role before looking for help, then will spend weeks deliberating, before deciding not to engage in a very low-cost trial. ?

6. People who sell anything else to consumers are not good customer-facing, part-time employees.