How to Start a Business

Writing by Susan Trumpbour

Design by Justin Negard

Animation by Isabella Aranda Garcia

As Gillespie puts it, failure is good initially, and it can be your best friend. The most successful entrepreneurs are the ones who can spot a dud, quickly learn from their mistakes and head back to the lab for a new plan.

It’s easy to fail; it’s harder to reflect and learn from your mistakes. Successful founders know how to learn; those who know it all are likely in for big disappointments.

“As an investor, it’s a red flag if I give feedback and they’re not listening,” Hauser adds. “That tells me they think they have it all figured out and don’t want advice.”

Interior designer Jennifer Gerken, who owned PORCH in Mount Kisco, says labs are also key for retail businesses.

“Understanding the market’s needs and picking the right spot is crucial,” she explains. “Invest time in thinking about this; I’m not sure I nailed this 100 percent when I opened PORCH. I wavered, wondering if my space was too big or too small. Looking back, it was probably too much space.”

Build a network and a community

Networking is essential, but it’s how you do it that matters.

“Networking to collect business cards or name drop is NOT the objective,” says Gillespie. “Instead, it’s to be curious and learn from others rather than trying to learn everything by yourself.”

One effective form of networking is to surround yourself with great mentors who will also help you navigate the path with insightful questions instead of cheerleading routines.

Let’s take a minute to reflect on this sage advice Gillespie often uses from a motivational speaker he likes: You are the average of the five people you hang with.

So if you’re spending time with a toddler, a bus driver, a nanny and a particularly chatty dog, you might not be in the best company for brainstorming about your new business (unless it’s a child/doggy daycare combo, of course). So boost your game by upgrading your circle. If you dream of starting a restaurant, for example, befriend a long-time waiter, a chef and even an owner. They might not launch the rocket with you, but they know the terrain.

Gillespie also believes in joining incubator or accelerator programs. In these groups, you’ll learn how to run your new business alongside other founders who can serve as great sounding boards for your ideas, concerns and questions.

Overall, groups, according to Hauser, are necessary; they’re the ultimate think tanks. She advises gathering experts who are passionate about what you’re diving into.

“When I launched my first book, ‘The Myth of the Nice Girl,’ I created a nice girl army,” she explains. “It was filled with young women who worked for me over the years. I started a Google Group with 150 women, and it was my way of communicating with them. I asked for support at my launch, PR boosts, people to write reviews, etc. Another great example is The Pound Ridge Working Moms Group, which I help run. Our policy is that you can promote something on the first of every month. It’s 1,300+ subscribers strong, giving local women business owners the opportunity to reach their target market.”

“I think about networking a lot,” Hauser continues. “There’s a relational and transactional piece, and both are critical. The relational piece is connecting with someone—going to a networking event or dinner and connecting on a deeper level. The transactional piece is just as important—swapping ideas and assistance; ‘I can help you with X. Can you help me with Y?’”

Yes, it takes effort and time, which is challenging when you’re starting a business, but Gerken says it’s worth it.

“I built friendly relationships with store owners on our block and within the area,” she says. “They became my family, and we would share advice and check in with each other often. This community group brought me joy and guided me on many levels.

Do you need a business plan? Eh, maybe not.

Crafting a business plan means jotting down your company’s grand dreams, strategies and the magical steps to get there. But is it essential?

“It depends,” says Hauser. “A formal business plan may not be necessary for smaller, self-funded ventures, but it is crucial for larger companies and those seeking external investors.”

What’s needed varies based on your context and goals. For instance, when Hauser launched PEOPLE.com, she implemented a comprehensive plan spanning three to five years.

“However, if you’re starting a venture like my new bookstore,” shares Hauser, “a formal plan might not be needed. The bookstore is experimental, and I am not bringing in outside investors; I’m just doing something to fulfill my bucket list and better the community.”

For smaller, self-funded businesses, a straightforward approach is fine.

Gillespie suggests a one-page visual business model that acts like a cheat sheet to answer the big questions: Who are your customers? Who is the competition? What unique magic do you bring to the table?

Money doesn’t guarantee success

Starting a business isn’t just about fundraising and throwing fancy launch parties. Money is required, and your own is advised.

“Many founders rush to raise capital, but I tell them to self-fund as long as they can,” Hauser advises. “Bringing investors on board adds a whole new layer of complexity. Yes, they may write a big check, but their expectations will be high, and the pressure will triple.”

It can’t be said enough: Choose your investors wisely. Hauser has seen mismatched partnerships lead to disagreements and, ultimately, the business’s failure.

“I always tell founders you should be as picky as the investors,” she says. “Investors are deciding if they want to invest in your company, and you need to decide if you want them in your life regularly.”

If it feels off and you’re dodging their calls like an ex, that’s a major red flag.

Final thoughts (that are worth thinking)

Each expert stressed these invaluable points, which they say often fly under the radar.

• You will underestimate how much cash you need. “It’s like building a house,” says Hauser. “Everything takes twice as long and costs twice as much. So, double everything and avoid the surprise.”
• Know what a typical revenue day looks like and understand what good, bad and break-even days are like, too. “I had no clue,” Gerken admits.
• Understand your strengths and know your weaknesses. “Space planning and interior design is not my thing,” admits Hauser. “Instead of stressing over how this will get done, I hired someone who loves decorating, so I could better focus on the things I excel at, like ordering great books and setting up author meets.”
• Don’t pitch your best product first. Gillespie says your first venture should not be your best idea; it should be the opportunity to learn those important business lessons so your better idea has a greater chance of becoming a successful business.
• Just because you’re starting a business with your BFF doesn’t mean it will always be dandy. “I’ve invested in companies with friends, and trust me, it can go south fast,” says Hauser. Partnerships are complicated, sometimes even requiring a therapist to mediate.
• Got grit? You need it. “Every day is different,” says Gerken. “There is so much you need to work through, push through, pivot and think about.”

As Hauser points out, the journey is just as important as the finish line. Don’t give up; savor every lesson and grab hold of every opportunity.

This article was published in the January/February 2025 edition of Connect to Northern Westchester.