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Entrepreneurs / Ask Entrepreneur

The Productivity Secrets of an Entrepreneur Whose First Business Idea Turned Into Multimillion-Dollar Company

The founder and CEO of Thumbtack looks to a quote from Bill Gates to help him stay focused on the long term.
The Productivity Secrets of an Entrepreneur Whose First Business Idea Turned Into Multimillion-Dollar Company
Image credit: Courtesy of Marco Zappacosta
- Entrepreneur Staff
Staff Writer. Covers media, tech, startups, culture and workplace trends.
10 min read

A Note From The Editor

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Editor's Note: Entrepreneur's "20 Questions" series features both established and up-and-coming entrepreneurs and asks them a number of questions about what makes them tick, their everyday success strategies and advice for aspiring founders.

So much of entrepreneurial success is about the connections you make.

Since 2009, Thumbtack founder and CEO Marco Zappacosta has grown his company by bringing together users and small-business professionals to work on projects ranging from dog training to appliance repair to wedding planning.

Since its launch, Thumbtack has gained a presence in all 50 states. The business now has a base of more than 250,000 active professionals providing more than a 1,000 kinds of services, with 5 million projects completed every year.

The company shared that it has helped to generate $1 billion in revenue for local businesses and it has raised more than $270 million in funding.

We caught up with Zappacosta to ask him 20 questions and find out what make him tick.

1. How do you start your day?
I start the day at 6 a.m. with a workout. Often my wife and I will work out together. It is a great way to wake up, get physical and sweat. I love it. Regardless of what I'm thinking about, it clears my mind.

2. How do you end your day?
Reading a book. So much of our lives can be dominated by emails, push notifications, Twitter and all that sort of stuff and a book is a great way for me to disconnect, explore something that I'm curious about and just relax a little bit.

3. What’s a book that changed your mind and why?
The Blank Slate by Steven Pinker really made made me realize how the brain was a system. It's something that could be studied and tried to be understood as an engineer might approach a physical system, and that got me excited. Neuroscience became a passion of mine. It really opened my eyes to that whole world.

4. What’s a book you always recommend and why?
I'm often talking to folks who are either inside of startups or thinking about it, and a book I recommend often is Apollo by Charles Murray. It's a history of the Apollo program and what is so staggering about that achievement is how fast it happened, how few people thought it was possible to happen in that time frame and just what a seed of human ingenuity it was. It's a gripping tale of human accomplishment and it's inspiring -- a reminder of what is possible.

Related: Health and Beauty Mogul Bobbi Brown Shares The Biggest Time Sucker -- and What You Can Do About It

5. What’s a strategy to keep focused?
The best strategy I've found is to have a shortlist of two to three items that are critical things that I need to get done. What it does is it gives me something to turn back to. I email myself the list. It is something to remind myself: OK, I've got the time, what should I prioritize and dig into? That lets me avoid the noise of what can be going on and keep my mind focused on a couple of critical things that need to get done in that time period.

6. When you were a kid what did you want to be when you grew up?
I wanted to be a research scientist and I was always sort of enamored by the idea of discovery and the process of running experiments and figuring things out. But then I spent a summer in a lab and realized that I was wrong and I did not actually want to do that. Intellectually, it was always a curiosity, a passion of mine. But then it was a reminder that just because it sounds good in a dream doesn't always make it true in reality.

7. What did you learn from the worst boss you ever had?
How important empathy is and recognizing that what's going on in your own skull isn't necessarily how the rest of the world sees it. [In my own business I'm always] trying to sort of have that perspective and maintain that perspective.

8. Who has influenced you most when it comes to how you approach your work?
My parents have definitely influenced me the most when it comes to how I approach my work. They're both entrepreneurs. In Silicon Valley and the narratives that emerge today it's all sort of crafted as these overnight successes. But what I saw my parents do was work hard on something for a decade or two and the amazing impact that that can have. That perseverance and commitment is super inspiring and something I try to take from them.

9. What’s a trip that changed you?
Both my parents are Italian. They immigrated in the 1970s. My extended family is back there, my cousins, aunts and uncles and grandparents. In the summers I would get shipped out and live with my grandparents and hang out with my cousins. Not only was it fun but I think the big thing was that it gave me a lot of perspective. Seeing those different places, cultures and attitudes. It just made me realize how big of a world it is out there. I didn't obviously think about it at the time but in retrospect I think that was incredibly formative.

Related: Shark Tank's Barbara Corcoran Explains Why You Must Make Time in Your Schedule For Fun

10. What inspires you?
I am inspired by our pros. I get to meet these folks who you have started their own companies and through their hustle and grit have achieved their dreams. To me, they are entrepreneurs just like us. It's so inspiring to hear that we get to play some part in their efforts.

11. What was your first business idea and what did you do with it?
I'm still working on it. Thumbtack is the first serious business idea I ever pursued. Going back to my parents inspiration, I hope I get to do this for my entire career. I'm not interested in flipping and moving on to the next thing. This is an idea that we can build on for decades and hopefully we have the opportunity to do that.

12. What was an early job that taught you something important or useful?
In middle school I was asked to help a soccer coach. The kids ended up being high schoolers. It was a weird thing being a coach to kids who were older than me. It was just a lesson in how you earn respect by being diligent and even in a scenario where it's not obvious that the audience will have natural respect for you. But it was a formative moment.

13. What’s the best advice you ever took?
Originally this was a Bill Gates quote. But somebody once told me that people overestimate what they can do in a year and underestimate what they can do in a decade. That has always really stuck with me. It's just this idea that with a very long time on the horizon, with a very big vision and dedication to keep after it day in and day out, you can get staggeringly far in a decade.

14. What's the worst piece of advice you ever got?
A lot of people told me Thumbtack wouldn't work. People would say small businesses aren't going to participate in a product like this. They're not going to sign up. You have to have a sales force or it won't work across all these categories. You can't launch all these cities at once. The advice was well-meaning and in many ways reasonable. But it was wrong. Thankfully we heeded it in as much as used it to test our own ideas but ultimately we just had the courage of our own conviction just kept going.

Related: She Was Told 'No' 100 Times. Now This 30-Year-Old Female Founder Runs a $1 Billion Business.

15. What’s a productivity tip you swear by?
I don't have any push notifications enabled for anything except text messages. In a world where so much can just come in at you, [you should] find a way to not let that distract and drown you. Being more deliberate and proactive about how you spend your time as opposed to being reactive. Even deleting apps like Facebook helps me focus.

16. Is there an app or tool you use in a surprising way to get things done or stay on track?
I started using voice memos as a way to sort of draft emails. I often have only five minutes between meetings, so instead of trying to pull out my phone and compose something I'll just record an audio memo. It's sort of the fastest way to create a first draft. Then I sit back at the computer, I tweak it a little bit and then it's good to go.

17. What does work-life balance mean to you?
I'll be honest, I kind of hate the concept. My reaction is because it makes it seem like one is good and the other is bad. My view is that we should be able to find purpose and excitement in both and draw energy from both and obviously they have different needs in different moments. But I try to take the long view, because in any one day or even one week it's hard to balance the needs that family or your life has with everything that your work needs from you. It starts with finding purpose and excitement and both. If you have that then balancing them is not a chore. It's easier and more natural.

18. How do you prevent burnout?
The biggest thing is being motivated by the impact that we're having rather than the specific problem we're solving or the project that I'm working on. Keeping the focus on the "why" is ultimately more motivating for me than the specific task that I'm doing in that moment. If there's ever sort of a moment where I'm tired, reminding myself of the "why" helps me. I try to talk to a few pros every week, get their stories and talk to them about what's going on.

19. When you’re faced with a creativity block, what’s your strategy to get innovating?
I'm an external processor and so I need conversation and debate with people to refine my own ideas and generate new ones. If I feel stuck, just getting people together in a room and spitballing and getting [ideas up] up on the whiteboard and debating something. For me that is the best way to spark new ideas and a way forward.

20. What are you learning now? Why is that important?
I'm about to be a dad. I've been thinking about that and reading some books but mainly just trying to talk to other dads to hear how they balance things. I'm really excited about it and it will be a whole new adventure.

I Was Living In Poverty When One Small Decision Started Making Me $5,000 a Week