It’s easy to get caught up in the romance of the first time — whether it’s love or entrepreneurship. But for so many founders, that initial startup is just the beginning.
Today, a panel of experts at Dell Women’s Entrepreneur Network (DWEN) event will examine the nuts and bolts of starting a successful second venture. The panel is part of the tech company’s annual conference, which began last night in its hometown of Austin and brings together female entrepreneurs from around the world.
The inspiration came from last year’s DWEN event during a session focused on scaling for the future: “Much of the conversation focused on the need to diversify and create multiple revenue streams in order to innovate and continue to grow,” says Jennifer “J.J.” Davis, executive director of global communications at Dell.
Today’s panel includes Catherine Graham, president of Toronto-based promotional products agency RIGHTSLEEVE and CEO of cloud-based business management software company commonsku, and Alexandra Wilkis Wilson, cofounder and head of strategic alliances for Gilt Groupe, among other high-profile female entrepreneurs.
“When you’re looking to start a second business, you should leverage your network in every possible way you possibly can,” says Graham.
We took her advice, asking a diverse group of women founders what they’d kept in mind when building their second — or sixth — businesses:
1. Wait until you have to pivot.
Starting a business can be hell on earth: You want to be so passionate about your idea that you have no choice but to do it. The idea for DailyWorth.com couldn’t have come at a worse time: Soapbxx.com, my 10-year-old web engineering company, was successful; I had a two-year-old and was pregnant with my second child. But if you’re obsessed with starting and building things, you have to strike when the idea hits you. And on the flip side, if you’re questioning whether it’s the right time, then maybe it isn’t.
— Amanda Steinberg, founder of digital media company DailyWorth.com
2. Ensure your first business is rock-solid.
One of the most challenging things about spinning out the second business is that the startup phase is all consuming. So make sure the original business is set up for success: Be very, very clear about its vision, its strategy, and about who is running the team to get you to your goals. You can’t over-communicate
— Catherine Graham, CEO of commonsku
3. Don’t expect overnight success. Life is all about embracing change and employing your skills into new areas to keep things fresh. After selling the marketing and communications consultancy that I started when I was 25, I wanted to move from advising businesses to building a brand of my own, deploying all the skills I’d learned so far. But [the transition] wasn’t instant: It really can take a couple of years to exit your first business, find the right idea to develop next, line up the team and get funding in place.
— Debbie Wosskow, Founder and CEO of Love Home Swap.
4. Capitalize on what went wrong the first time.
The easiest part of starting a second business is having the wisdom and experience to know what NOT to do. I had 40 angel investors in my first company, many of whom had no knowledge of our industry, and I spent much of my time managing them. The second time around, I made sure I only had five angel investors, all of whom could add value to my business in some way, before a series A round.
— Ruma Bose, principal at Ohana Capital
5. Take your time building buzz.
Before we launched Zady.com 10 months ago, one of Warby Parker’s founders told us: “You can only launch your brand once.” We planned for our release 90 days in advance, creating a “coming soon” website with just enough detail—but not enough to write a story about Zady. Eventually we did speak to a top journalist, which resulted in a cover story in August of 2013. From there, we were off to the races.
— Soraya Darabi, co-founder of Zady.com
6. Maintain a first-timer’s enthusiasm
A second business is easier in some ways and more difficult in others, just as a second child is: You may have fewer stumbles, but you still have to wake up at 2AM and change the diapers. Since the newness won’t be there [the second time around], you have to really, truly be as fired up—if not more so—about your concept.
— Carolyn Rodz, founder of Market Mentor