Why It’s Crucial to Go All In On Yourself As an Entrepreneur

In December 2022, my co-founder and I closed a friends and family seed round for Popsmith, raising US$1.53 million from 84 investors in under 45 days during arguably one of the worst times to raise money since 2008. 

I’ve founded several companies over the past 20 years, but this was my first time raising money. Over the years, I have learned a lot of important lessons as a member of Entrepreneurs’ Organization, Million Dollar Sellers and eCommerceFuel.

Arguably the most important lesson I learned is how critical it is to go all in on yourself as an entrepreneur. After all, if you don’t believe in yourself, how can you expect anyone else to?

Working-class roots taught me grit

I come from an uneducated immigrant working-class family. We lived in Coney Island government-subsidized housing for the first few years of my life. My parents divorced when I was young, and we fell into poverty. We had no health insurance; we shopped with food stamps. 

My mom was left to raise two young boys essentially on her own with very little support. She did everything she could to make ends meet — cutting hair during the week and making and selling jewelry at night and on weekends. I spent many late nights alongside her, piecing together earrings and pendants on a folding table in our tiny apartment. We would wake up pre-dawn every Sunday, drive to the local swap meet, set up our booth, and sell our goods until sundown. Talk about grit! She had it in spades, and I picked it up from her.

We were homeless for a stretch. My kid brother and I slept in sleeping bags on the floor of the hair salon where our mom worked while she took the couch. We showered twice a week at a local hostel. Meals were either fast food or cooked in a microwave.  

I had a very low sense of self-worth growing up. I was overweight and debilitatingly shy. I had few friends and very little guidance. I was bullied and teased incessantly. I was largely ignored, which stung the most. 

Bootstrapping by age 12

I learned self-reliance early. I discovered that I had a knack for business at a very young age. Looking back, it seems like entrepreneurship was my destiny.

I started selling gumballs at school when I was 12 years old. I traded sports cards, delivered pizza, worked in fast food restaurants, waited tables, sold used cars, flipped burgers, and ran a vending route. I put myself through school and was the first person in my family to earn a college degree (and a high school diploma). 

Work became my salvation, and I slowly built myself up, mentally and financially. 

I started Gumballs.com at 21 years old with $2,400 — my entire life’s savings at the time. My kid brother, Ron, gave me $1,700 to help out, nearly everything he had, and against my wishes. I cried when I got that check. 

My initial financial goals were humble: I needed to make US$3,000 per month in profit, enough to cover my basic living expenses, including a $10 per day food budget and rent for the trailer where I lived at the time. 

My goals — and my self-confidence — grew as my business grew; 100-hour workweeks were the norm. I set a lofty goal: To become a millionaire by age 30. I got there at age 26, yet I still felt I had more to prove to myself. 

I went on to found a half-dozen additional businesses, all 100% bootstrapped and self-funded. Some failed; some succeeded. Life and business can beat you up. Developing a tough skin while maintaining a soft heart becomes essential. 

Today, I am the culmination of a lifetime of learning, pain, therapy, self-exploration, coaching, failures and triumphs. Many men suffer from imposter syndrome, including myself. Through patience and grace, I slowly realized that I am no longer that scared little boy who everyone ignored, ill-fated to follow in my father’s footsteps and repeat his transgressions. I know now that I am a competent man, worthy of love and support, a person who gives back to his community and is capable of leading a team toward success. 

Betting on myself

A few years ago, I divested myself of all of my businesses to go all-in on what would eventually become Popsmith, investing millions of my own capital. 

I wouldn’t ask my friends and family to bet on something I’m not willing to make a big bet on myself.  

People asked me, “Why raise money?” That’s a valid question. Between my own capital and debt, I didn’t need to raise money. I chose to do so, in part, to mitigate risk.

But the larger reason was that I was excited to have my closest friends and family alongside me on this journey. I wanted us to win together. 

Can Popsmith fail? Definitely. Business is hard. A lot can go wrong. 

But I believe deeply in the company, the incredible team we’re building, and in myself.  

I think we’re stacking the odds heavily in our favor to win. And after my friends and family invested in my company — which literally brought tears of gratitude to my eyes — I can’t wait to prove to them how heavily invested I am in making our shared future a tremendous success!

Contributed to EO by Tal Moore, an EO Los Angeles member who is founder and CEO of Popsmith. A version of this post first appeared on Tal Moore’s LinkedIn page and is reposted here with permission.

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