By Jason Fell and Stephanie Schomer, Entrepreneur
How do you know when the time is right?
It’s a constant question throughout the entrepreneurial journey. When is it the right time to launch your business? When is it the right time to grow? When is it the right time to make your first big hire? When do you know it’s time to fire? When should you consider raising capital? When should you hang on tight to your bootstrapped company? There’s no single answer to any of these questions -- and there’s no exact science to finding the answer that will best boost your business. But on the following pages, eight entrepreneurs discuss their own big decisions -- some made at the right time, some at the wrong time -- the instinct they followed (or ignored), and the lessons they learned.
The Right Time to Launch
When you’re worthy of consumers’ trust.
Back in 2016, Kal Vepuri’s product was far from perfect. But maybe that didn’t matter, he thought. “Our original approach was the classic startup way of thinking: Get an MVP to market, and work out the kinks later,” he says. Then he reconsidered.
Vepuri’s company is called Hero, and its goal is to help people manage their medications. It does this with software as well as a pill dispenser that releases the right doses at the right times. Vepuri came to realize that, because of the medical nature of his product, he couldn’t embrace the traditional hiccups of an MVP release. “The product had to be incredibly safe,” he says. “It had to be validated way beyond what a typical hardware product needs.”
So he hit the brakes and told his team that launch would wait until they were truly ready; a small private beta would still provide them with enough feedback to iterate. “It actually reinvigorated the team,” he says. “It allowed us to turn our focus back to the user and the patient and the caregiver.”
When Hero finally launched in 2018, the startup found a passionate consumer base -- buoyed by enthusiastic beta users -- and Vepuri knew he’d made the right call. “We delivered a seamless experience.”
The Wrong Time to Launch
Before you can pay off on your promise.
When kitchenware brand Material was preparing to launch, its founders had two options: Wait until March 2018, when product would be ready to ship, or announce the brand four months earlier, in November, to drum up press ahead of the holiday season and hope eager customers would preorder the product.
They chose the latter -- so that fall, cofounders Eunice Byun and Dave Nguyen started introducing the brand to editors at various publications and websites. The product was well-received, but the timing was off: Some journalists covered the preorder buzz right away, in November. Others waited until March, publishing stories when customers could actually buy and receive the products. And that news split effectively turned the volume down on the brand’s launch story.
“It diluted our opportunity,” Byun says. “If we had waited [until March] on the press side, we would have seen more consolidation of those moments. When you’re trying to be as nimble and resourceful as possible, you have to connect those dots between great press and effective acquisition strategies.”
The strategy wasn’t an entire flop, though. During the months leading up to its official launch, Material did bring in enough orders to sell out of its initial product run. But Byun regrets missing out on making a really big splash. “If you have something that’s going to get a great response, sit on it a little bit,” she says. “Build up some of that allure and mystique, and translate that into momentum.”
The Right Time to Grow
When the market wants what you’re selling.
When Jaime Schmidt started selling Schmidt’s Naturals -- homemade body-care products -- at a farmers’ market in Portland, Oreg., in 2010, she expected to unload a few bars of deodorant and start building a customer base. But she got so much more than that.
“Retailers were asking for line sheets and brochures,” Schmidt says. She had none, but she knew she couldn’t waste the opportunity. “I quickly recognized the enthusiasm from the community and the serious business potential in front of me, and I dove all in without a formal business plan.”
She scrambled to create sales materials and the following week showed up at the market ready to make a deal. With a few small orders in hand from local retailers Alberta Cooperative and New Seasons, she then focused on scaling production, developing a growth plan, and building strategic partnerships that would help her grow from making 20-unit batches in her kitchen to today, where she’s fulfilling 400,000-unit orders for Costco.
“Our timing was perfect,” says Schmidt. “My approach has always been to say yes now, then figure out how. Oftentimes, it’s your risk tolerance as a business owner that will dictate your success.”
The Wrong Time to Grow
When the market isn’t ready for you.
Andrew Pudalov was sure he’d created a hit. It was 2004, and he’d opened a restaurant called Rush Bowls that sold fruit-based bowls blended with proteins and vitamins, then topped with organic granola and honey. It was perfect for his health-conscious community of Boulder, Colo., and consumers even started ordering bowls to take home and save for later. That gave Pudalov an idea: He could make a frozen version and sell it in high-end supermarkets.
Whole Foods and others were intrigued by this and started selling the frozen versions of his bowls locally in 2010. Sales were promising, so Rush Bowls agreed to quickly expand across 40 states -- and that’s where the problem began. “Since our bowls were the first of their kind in the wholesale market, it was challenging and costly to educate the consumer [about blended frozen fruit bowls and how to prepare them],” Pudalov says.
A better launch plan, he suspects, would have been to target distribution to hospitals and health clubs. “We were beginning to gain traction there,” he says. It may have also been wiser to be more strategic about geography, starting with markets like Boulder, where consumers are already primed for his kind of product.
In 2018, a year after Amazon bought Whole Foods, Rush Bowls decided it needed a new strategy. It pulled its products out of supermarkets and returned to its restaurant focus, which Pudalov now franchises -- but at a measured rate. “Be cautious of a very rapid expansion,” he says.
The Right Time to Hire
When you know exactly the help you need.
In 2015, Iva Pawling and Tim Morse were at a crossroads. Their company, Richer Poorer, had spent its first five years selling socks and boxers, and was now expanding into a new category: men’s T-shirts. The new products proved an instant hit, so Pawling pushed her staff to introduce the women’s version in just a matter of months.
It was a heavy lift for the 20-person team, and they quickly fell behind schedule. Then they grew frustrated with Pawling and Morse, who didn’t have the bandwidth to effectively lead them through the project.
“I was focused on the creative functions of the business, [Tim] was focused on revenue growth, and neither of us was great at managing people,” Pawling says. They realized they had to grow…and so they identified the most important pain point that a new hire could solve. The answer: They brought on a general manager to oversee operations.
The results were immediate. “Having an intermediary between the founders and the whole team has given us the ability to create a culture that is transparent and truly discusses all issues head-on,” Pawling says. “It’s created a healthier organization.” It’s led to more growth, too. In addition to tees and socks, the company now sells sweats, tanks, dresses, and bralettes, and is approaching $13 million in revenue.
The Wrong Time to Hire
When you can afford only the next-best thing.
Stephen Valand opened Brooklyn Brew Shop with Erica Shea in 2009, with the goal of creating and selling stylish, easy-to-use beer-making kits for stove-top brewing. They decided to staff up early, but they had a tiny budget. (The company was launched with just $4,000.) So that meant they could hire from only a limited talent pool of inexperienced young folks.
Soon they were dealing with an entirely new set of problems.
“People who come into a job with little experience can be great at the day-to-day duties and the tasks assigned to them,” Valand says. “But you’ll always be limited by your bandwidth as a leader. There have definitely been days spent showing young people how to send full shipping containers to Europe and explaining the very real ramifications of Brexit as if it were a poli-sci class.”
Today, the decade-old business is approaching $2 million in revenue and has expanded to a production facility in upstate New York. But the founders still feel the ripple effect of their original quick-to-hire strategy and wonder what would have happened had they waited until they could afford experienced, veteran hires. “When you’re training your 12th marketing assistant in 10 years how to use Mailchimp, you know there must be a better way to build a team,” Valand says.
The Right Time to Raise Money
When you’ve done your homework.
Ariane Goldman tried to raise money for her maternity-clothing startup, Hatch -- and the timing was all wrong. “I was eight months pregnant, overwhelmed, and just didn’t have the confidence,” she says. “And I didn’t need the money to survive at that point.”
So she hit pause, gave herself time to relish the birth of her newborn, and went back to work with a clearer mission. Goldman knew she wanted to add a skin-care line and push into brick-and-mortar development; that would require an influx of capital. It would also require more help.
“I’m an entrepreneur, and I have a vision, but spreadsheets? Not my greatest strength,” Goldman says. She set out to find a business-minded partner and ultimately hired a friend (and customer) to be the yin to her yang. “She’s good at all the stuff I’m not into,” Goldman says.
That included prepping for a fund-raise. Eighteen months after her initial attempt, Goldman and her new COO approached investors. And this time, they were overprepared.
“We nailed it,” Goldman says. “I don’t mean to sound gross, but we didn’t even have to put a deck together. We raised money on the pitch and the numbers.”
The Wrong Time to Raise Money
When everything feels new and exciting.
In 2017, Trinity Mouzon Wofford launched wellness brand Golde with a powdered turmeric tonic that may boost immunity and decrease inflammation. Along with her cofounder, Issey Kobori, Wofford bootstrapped the operation and envisioned a brand built on slow and steady growth -- one that could make holistic health accessible and affordable.
Customers loved it, media covered it, and Golde was soon fielding inquiries from the likes of Goop and Nordstrom. Then investors reached out. “We kind of got thrust into the world of venture capital,” Wofford says. “It’s very easy to get swept up in that culture.”
Wofford and Kobori felt they’d been given an opportunity they couldn’t turn down, so they spent months meeting with more than 30 potential investors -- and even received a handful of offers. “I was being told this classic tale: It’s better to own a small chunk of a big company than a big chunk of a small company,” she says. “I accepted that for a while -- I’m young, I’m a woman of color in a space that doesn’t have a lot of people that look like me.”
But then she took a step back. Did she really want to give away so much? Just because investors were calling didn’t mean she was obligated to say yes. “I think in our guts, we knew early on what the right decision was. It just took time to let ourselves tap into that.”
Now Wofford and Kobori are growing at their own pace, and they plan to reconsider raising capital when -- and if -- the timing feels right. After all, they’ve already put in the legwork. “We met some incredible investors along the way,” Wofford says. “If we jump back into that world in a year or two, I’d love to find a way to work with them.”
