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Making the Leap: A Founder's To-Do List

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Making the leap into starting your own business is a brave and bold move, and everyone's path is different. There are plenty of things I wish I'd known when I decided to quit my position at IBM and work on the idea that later became TaskRabbit. Maybe that's why one of the things I cherish most about being a founder and CEO is the opportunity to offer advice to new entrepreneurs. Here's my ultimate to-do list for new and aspiring founders.

1. Let go. Life is like the monkey bars, you have to let go to move forward. Once you make the decision to leap into entrepreneurship, be sure to loosen your grasp on old concepts so you can swing your way to new ones.

2. Talk to everyone you know and everyone you meet about your idea. Doing this will help you gather feedback, identify problems and action steps, and bring the right people into your orbit. This type of hands-on networking still works. I met Scott Griffith, the CEO of Zipcar who helped propel my company in a huge way, through a mutual acquaintance I'd chatted up about TaskRabbit.

3. Trust your gut. It's important to gather information and consider other points of view, but your gut calls will make or break your business. Learn to bet on yourself and have confidence in your own decisions. No one knows your business better than you.

4. Be passionate about the problem you're trying to solve. Believing the world will be more awesome when your company succeeds gives you an edge -- don't lose it. Knowing that TaskRabbit is poised to revolutionize work as we know it is like rocket fuel to me.

5. Figure out what your personal runway looks like. Budget out how much money you can actually live on in the next 6, 12, and 18 months. Be really honest with yourself about how much you're willing to change your lifestyle. Are you willing to go full ramen?

6. Be scrappy and lean. And don't forget to test everything you can.

7. Build a support community full of innovators, creators, darers, and doers. Surrounding yourself with people who are actively and enthusiastically working toward their best futures will keep you moving toward your own goals.

8. Find advisers. Assemble a panel of people who know the things you don't know, who've made the kinds of mistakes you'd like to avoid, and who are looking at your business from perspectives you don't have -- and get them involved every step of the way.

9. Set big goals, with small action steps. Your goals can be big, hairy, and audacious but the steps you take to get there should be specific and actionable. At TaskRabbit, we're looking to revolutionize the way people think about work -- pretty audacious -- but we started at the hyper-local level and then iterated from there.

10. Use the resources in front of you, not the investment round you're sure is around the corner. This one's important. You may think your idea is worth millions, you may even have someone interested in writing that check, but don't start spending like a Mega Millions winner. It'll only distract you.

11. Give yourself deadlines. Being your own boss doesn't mean you aren't accountable to anyone. Just the opposite. It means you're accountable to everyone. Your employees, your customers, your investors, and yourself. Set deadlines to keep yourself in check.

12. Make mistakes. On purpose (and by accident).

13. Figure out what your stories are. Whether it's your origin story, an inspirational customer case study, or the story of how your business will disrupt its space, you'll be telling it often. Take some time to isolate the best story lines in your company's narrative. You'll use these again and again for everything from PR to elevator pitches to defining your company's core values.

14. Keep a finger on the pulse of your industry. Stay in the loop of every topic area in, or adjacent to, your field. This will do a lot more than simply keep you informed, it will also give you the necessary context you need to understand where your own company fits.

15. Blog. Not only is a company blog an excellent engagement tool, it's a vehicle for press releases, an anchor for your social networking efforts, and added value for partner relationships. If you're in the very early stages of your business, blogging about your experience to an audience also adds a layer of built-in accountability.

16. Get into a co-working space. Working from a co-working space gives you access to so many resources -- not least of which includes the networks and experiences of your fellow founders.

17. Get out of the house. Potential employees, investors, partners, and members of the press aren't going to wander into your home and ask if they can help make your business succeed. You need to leave the house to find those opportunities. And maybe hit the gym while you're out there -- you can't grow a healthy business if you aren't taking care of yourself.

18. Embrace the business side of things. Even if you're more of an "idea person," "creative type," or "product guy," you need to understand the business mechanics that make your business viable. Take time to learn about financial modeling, creating a pitch deck, investor relations, competitor analysis, and marketing. You don't need an MBA to master this stuff!

19. Choose partners and early employees wisely. I've said it before and I'll say it again, your team members will define your company culture. Don't bring people on board lightly. Consider their character, their working style, and the contributions they'll be able to make now and into the future.

20. Push your company as far as you can every single day.