What Do You Do After You’re an Entrepreneur?

Do it again.

“So…now what do I do?” That’s the question I was left with after selling my company, Bucket, last year. I had spent the last few years giving everything to the company, working to solve trip planning with travel technology.

Like any startup, we had many ups and downs, many within the same hour. Doing a startup was like getting punched in the face all the time, you keep getting up, but each time it wears you down.

The beginning of 2016 was tough. We pulled off an acquisition, but it had taken a toll on me. I was tired. Exhausted. Pooped. All I wanted to do was report to someone, be surrounded by smart people that I didn’t have to recruit, and feel a sense of stability.

You can feel a bit lost after moving on from something you’ve built, so I’m sharing my journey through transition — my approach, my zig-zagged exploration through multiple roles and various companies, and the advice that was shared with me — for all the entrepreneurs and people who are figuring out what’s next. Hopefully this eases your own journey.

I’ve always found you learn a lot by chatting with people who have been in your shoes, so I spent a few months tracking down former entrepreneurs and those that worked with entrepreneurs to get some advice.

Here’s what they said:

“So what do you do after you’re an entrepreneur?” I asked my friend and partner at VC firm Andreessen Horowitz, Connie Chan. “Do it again” she said.

But I was tired, firefighting 24/7 for years on end. I wasn’t ready to launch another startup; I didn’t want to.

I was your model employee: a diligent worker, a great problem solver, and ready to do exactly what you asked without question. I was going to be the best gosh darn report you ever had!

“You’re still an entrepreneur, you’re just in between things,” Ilya Sukhar, a friend and partner from Matrix Partners said. But I was dubious. I could go back to a structured org, right?

“Go back to what you were doing before,” my startup mentor and friend, Sam Odio told me. For him, that was product. For me, that was product marketing and marketing.

I felt good about what I could contribute going back to a more established company — having been at a high-growth company like Facebook in its early years from 200–2500 people, and then having built something from scratch and worked on every facet from concept, design, UX, marketing, operations, fundraising, partnerships, recruiting, leadership etc.

So I set off to find out what opportunities were out there. I started by looking for positions online and then asking friends to refer me.

“Don’t leave entrepreneurship. You have it,” Sebastien de Halleux, former Playfish COO and now COO of Saildrone told me. “But if you really want to explore, the roles you’re looking for aren’t listed on a website.”

I did want to explore, and he was right about where to look.

I was looking for something senior that spanned multiple categories. So I started setting up meetings with CEOs and VPs, and helped them understand what value I could provide to the organization.

But what exactly was that value?

I had done a little bit of everything over the years. I was a strong generalist, and whatever I didn’t know, I worked really hard to learn. However, I was not quite as specialized as someone who had been doing the same job for 10 years.

People initially pushed me towards Product where most entrepreneurs end up at larger organizations. Many big companies position this as a “mini-CEO” for your organization, touching all facets of the company and driving the vision of the product you’re working on.

But it wasn’t really like being a CEO. At a bigger company, the role is much more tactical, and ultimately you don’t have the final say. Your product could end up being beautiful, or an ugly mish-mash of a lot of bad ideas. Maybe VP of Product would rock, but most PM jobs felt more like project managers, rather than product managers.

So I explored my other skillsets. My background was in marketing, and I loved marketing. I’d also found along the way that I was surprisingly good at Partnerships, teasing out the exact right partner, helping get them excited about our joint vision, and managing that relationship through.

So I explored there too. I found some product marketing and partnership roles that were exciting to me, and I talked my way into interviews often leveraging a higher position to get me in the door.

Here, it was more difficult. When I spoke to CEOs and VPs of the companies, there was strong enthusiasm to have an entrepreneur join the org. Someone that you could throw into almost any situation and they’d be able to make sense of it.

The farther down the chain I got, the less they understood the value that I could provide. My resume didn’t look like others they were looking at. I didn’t have “10 years of product marketing experience.” Rather, I had a few years and a lot of experience launching products from scratch and a smorgasbord of other skills.

I’d get questions like:

“Can you report to anyone?”

“Have you ever had a manager?”

“Can you give me an example of a situation where you didn’t have final say and how you convinced people to do it your way?”

My answers were yes, yes, and yes! But it was more confusing to them than anything else.

Of course I can report to someone else, but they do have to be quite competent — I’ve seen enough things fall away on mismanaged leadership.

Of course I’ve had managers. I was at Facebook for 4.5 years and I’m not Mark Zuckerberg.

Of course I’ve been in many situations where you don’t have final say. Even as CEO you’re constantly negotiating with your investors, team, partners, and more. You have the illusions of control, but often no control at all.

As you can imagine, these conversations spanned months and looked something like this, as I worked my way from the top into the right orgs:

High Level Exec (1–2 months for a meeting) → Hiring Manager (another 1–2 months for a meeting) → Figuring Out Role (2 weeks to a month) → Recruiter (2 weeks — 1 month for a meeting) → First Screen (2 weeks — 1 month for meeting, sometimes this was skipped since I’d already talked to the hiring manager) → Full Panel (2 weeks — 1 month for meeting) → Offer (2 weeks - 1 month)

Long story short, it took many months to work through any larger organization. And over time, I regained my energy. If you’ve ever met an entrepreneur, they build because they can, and they’re incredibly impatient. They’re driven to learn, to grow, to go full force into moving heaven and earth to solve a problem.

So in the midst of all this, I started tinkering. I’m a kinesthetic learner, and I think the best way to learn anything is just to get in there and figure it out. I’d always had a desire to learn more about building physical products, and there were some problems for professional women that I had been sitting on for years and still hadn’t found a better solution.

As a female professional, I felt that I often had to choose between things that were beautiful and expensive with no functionality, or things that were practical and comfortable, but made me look young and unsophisticated.

So I started building Tara&Co, reimagining products for real women. Within 6 weeks, I had recruited a designer with 15 years of experience and we had built our first prototype. The adrenaline of doing it all again was amazing.

But this time, I was even better. I could make decisions in an eighth of the time, I knew how to prioritize, where to put my resources, and how to jam and build as fast as I could. I was only limited by how many hours I had in a day.

Ultimately, I had a few offers that I was excited about, but none could compare to the awesomeness that came with building your own thing again.

So here I am, doing it again. Maybe I’m crazy, maybe I’m just an entrepreneur for life.

If you want to follow along with our adventure at Tara&Co, subscribe here. We’re launching our first product, a stylish and convertible bag for women on-the-go, on Indiegogo on May 9th.

We’re also hosting a launch event and a celebration of women on May 10th in San Francisco. So stop on by!

And with that, I leave you with these three thoughts:

  1. After a grueling experience, take time to yourself if you can afford it. Your energy level will recover and what you will want will evolve over time.
  2. If you leave entrepreneurs to their own devices for too long, they’ll build something.
  3. Embrace who you are. You may fight who you are for money/fame/stability/time/social pressure/friends/fear/love, but at the end of the day you’ll end up in the same place, it just might take you longer to get there.

I’ve embraced who I am.

So what do you do after you’re an entrepreneur? My answer is, do it again.

*Special thanks everyone who took time to chat with me during this process including: Adora Cheung, Amitt Mahajan, Andrew “Boz” Bosworth, CeCe Cheng, Christopher Fong, Clara Shih, Connie Chan, Dave Munichiello, Deborah Liu, Eurie Kim, Ilya Sukhar, Ime Archibong, Jeff Clavier, Jonathan Ehrlich, Jonathan Heiliger, Jonathan Hsu, Kent Goldman, Mike Vernal, Nate Blecharczyk, Patrick S. Chung, Pete Kooman, Sam Odio, Sebastien de Halluex, Terrence Rohan, and Vivek Patel.