Editor's Note: This story is part of the series "Entrepreneurship: Square One and Beyond," a Next Avenue initiative made possible by the Richard M. Schulze Family Foundation and EIX, the Entrepreneur Innovation Exchange
Many bring decades of professional experience, resilience, and hard-earned perspective to their startups. But the first year of business is often unpredictable, a reality that can feel especially daunting later in life, when the stakes are higher and there's less room for error.
From a paint-and-sip business founder, to a wealth management firm CEO, to an overnight oats company founder, three entrepreneurs over age 50 reflect, in their own words, on what their first year in business taught them: what surprised them most, the lessons they wish they'd known earlier, and the unexpected advantages that came with starting something new later in life.
Jeff Freedman, Co-Founder Dozy Oats
I started my own ad agency when I was in my 30s, and I did that for 17 years before I sold the business in 2019. In 2020, during the COVID-19 pandemic, I was home and would often make overnight oats. I had no plans to start another business. But I got tired of making oats every morning. I thought there must be a company where I could buy them.
When I couldn't find what I wanted on the market, it seemed like overnight oats were going to be my next project. I'd always wanted to create my own brand after helping so many companies create and fine-tune theirs. I was still working full-time for the company that bought my ad agency, so I brought Dana, my cousin, in as a partner on the oats idea. He also had a full-time job, so I figured we could divide and conquer. It was a passion project at first, something we worked on at night and on the weekends.
In late October 2022, we launched a Kickstarter fundraising campign. We pre-sold a ton of oats to our friends and family and raised $10,000. It's not a huge amount, but the idea was to get a little bit of awareness around our product. Then we started the business in 2023 when I was 54 years old. During our first year, it was really helpful for me to spend time meeting people in the industry and learning as much as I could. I didn't know what I didn't know, and it turned out I didn't know a lot. I didn't know what went into nutrition labels, about certificates of analysis, or about all the food safety rules and regulations. Your first year is all about learning and making connections.
I leaned on a CEO group I was in for those connections. If you can afford to join a CEO group—they can be pretty expensive—I highly recommend it. The group I was in had top-notch speakers, and your CEO counterparts hold you accountable. They aren't afraid to be honest with you. I also got a lot of support from our partners and suppliers. Get close to your suppliers, ask them questions, and let them teach you.
“If you start a business, to be successful you've got to go all 'oat.'”
Last December, I left my full-time job and put all my focus on Dozy Oats That was definitely another lesson I've learned; if you start a business, to be successful you've got to go all 'oat.' Working full-time jobs the first few years, my cousin and I did what we could and covered the basics, but certainly we could have grown (and learned) faster if we had gone all out and put more time and effort into it. Now that I'm able to put more time in, I can do more to explore additional distribution channels, review data and analytics, test more marketing and advertising, conduct research, improve our website and the customer experience, and test and launch new products. Two other pieces of advice I'd give for your first year: never make assumptions and always very pay close attention to your cash flow.
Jenny Zhan, Founder and CEO of Beyond Holding Co., LTD
My career has been in financial services. For 10 years, I was a portfolio manager and managing director for GMO, an asset management company. I always had the desire to be an entrepreneur, but back then I lacked the confidence to do it.
It was in late 2019 when I started Beyond Holding, a real estate investment and wealth management firm. Not long after that, the COVID-19 pandemic happened. The business environment suddenly changed, and along with it, my business plan. The lesson I learned from my first year was that you have to be ready to pivot quickly and adjust. You always have to have a Plan B and a Plan C, and you need to be prepared to switch things up and move in another direction. That's very important.
“You've likely already established networks for yourself, and you've probably already learned from many mistakes over the years.”
At Beyond Holding, the commercial real estate projects that we initially emphasized were not feasible anymore after the pandemic changed everything. So, we decided to pivot into single-family homes. This taught me that you have to be willing to abandon certain ideas that you initially thought were great ones.
I did find that starting a business after age 50 definitely had some advantages. You've likely already established networks for yourself, and you've probably already learned from many mistakes over the years. When you're in your 50s and older, at least for me, it also feels much easier to accept that the world is always changing, and you're going to have to adapt because you've likely done it many times before in one form or another.
As an entrepreneur, it's also critical to always be learning. You can't passively adapt to the business environment; you have to practice forward thinking. You always need to think about what business will be like in the next five years. This is the AI era, and it's forcing us to change. So, no matter what age you are, never stop learning and picking up new abilities. I'd also say, spend time exercising. Especially when you're over age 50, you really have to appreciate and nurture your health.
Cathy Deano, Founder of Painting with a Twist
I was 55 when I started Painting with a Twist with Renee, a friend of mine who's 15 years younger than me, after Hurricane Katrina. We wanted to start a happy business. The idea behind paint-and-sip wasn't entirely new, it had been done here and there before. But it had never been put into a really successful system.
We opened a little store in Mandeville, Louisiana. It was a place where women could gather and enjoy each other's company and have a drink and paint. It was only going to be one store. But the business really hit a chord. We had Renee's mom run a second location in New Orleans, and that gave us a lot more exposure.
Within about three weeks, we had customers coming to us saying they wanted to open Painting with a Twist locations in other cities across the U.S. That's when we knew we were really onto something. But we didn't know anything about franchising. What helped us was talking to people at another local franchise, PJ's Coffee. Renee had been drinking coffee at her local PJ's for about 15 years. So, she said, "Let's go talk to them," and that's what we did. They mentored us through what we didn't know.
Originally, we named our company Corks & Canvas, but then we ended up really wanting to do children's programs and work with schools. Because the name was tied to alcohol, we made the difficult decision to rebrand two years in. We also joined the International Franchise Association, or IFA, to help us with franchising, which I would recommend. They had a great mentoring program.
“I came into it thinking more about how our business can help other families, and not solely about the return on investment.”
One thing about starting a business later in life is that I came into it thinking more about how our business can help other families, and not solely about the return on investment. One challenge we faced early on was that we oversold franchises. There were so many people who wanted to open one of our stores. They're sitting there with a $25,000 check for you, and it's tempting when you're growing, and money is tight, so you say yes to everyone. The lesson there is, don't get ahead of yourself. You really need to be very strategic about expansion and consider your demographics.
For first-year advice, I'd also say surround yourself with people smarter than you and stay ethical. Start giving back to your community. It's a good thing to do, and it's good for business. We have a very robust give-back component to our business, and I highly recommend doing that as soon as you can afford it.
From Wounded Warrior Project to the Make-A-Wish Foundation, all of our franchises combined have donated over $10 million to non-profits, and I'm very, very proud of that. Last year, Twist Brands LLC, which I co-founded to expand our impact, acquired Pinot's Palette, Painting with a Twist's largest competitor. Now, at 72, I'm still actively leading our brand.