
A little while ago a colleague was debating leaving his job to build a startup and reached out to ask my advice. I sent a string of texts but realized that I really should sit down and think this out.
It’s been just over 8 years since I took my big risk in life to quit my job and build a startup. Everyone always tells me how brave I was to do it or how much they admire me for taking the risk. I know that I needed to take a shot. I needed to know if my dream could become reality. The risk of making it to the end of my life and not knowing, is greater than what happened. I’m just not good with regret.
But looking back, I realize I did the risk prep all wrong. I remember reading so many VCs who professed that they wanted to see a ‘burn the ships’ commitment from founders. It makes sense, if someone invests in you as their full time job, you should also be doing this full time. As painful as it was to not have a paycheck for 28 months, this was actually the right decision. I was all-in. I really thought that my investment and commitment was different from the part time thing I had been doing the previous years. I figured if I failed, I would figure something out. Failed founders find second careers all the time.
And that was the problem. Given how many startups fail, I should have been much more specific about my backup plan. While it seemed that having a specific plan would undercut my commitment to TheMissionZone, I now have to contend that Plan B would have made me better at Plan A. I would have been more methodical, less desperate.
I spent a lot of time with other desperate startups in and around Boston. It’s possible that I could have gotten a job with another startup after I closed TheMissionZone. But I was liquidating my 401k to live and pay for the company. When I was finally done, I needed a paycheck. One big enough with a ‘company match’ to make up for time spent. I quickly realized I built the wrong network outside of BigCo. Not good for when I wanted to get back in the workforce.
Before I left my full time job, I was gung-ho startup culture. I was learning about VC’s; reading blogs, following Twitter, commenting, generating thought leadership content, building my startup brand. I was good at my full-time job and I did it well. But I wasn’t spending 10 hours on the weekend building skills, network and credentials to get ahead in my career. That would have proved useful when I came back.
8 years later and I’m behind my peers. My network all moved past me. I’m well beyond taking another big risk in startup land. I’m still recovering. My struggle is that I have an entrepreneurial spirit in a place where that doesn’t really help me.
So what would I do differently? What do I recommend if you are ready to take the plunge?
- Smarter VC targeting – While in BigCo, at least a year before leaving, scour the VC landscape and ONLY follow the ones that might be interested in your company, but NOT in ones that have invested in a competitor. Brad Feld, Jeff Bussgang, Ben Horowitz, Mark Suster, Fred Wilson (I know I’m dating myself) all really smart…and have zero interest in a real-world immersive experience platform. Duh Josh. It doesn’t matter how smart they are, how good their advice/content/blog is or how much you might think you would click with them. Start engaging with potential investors before you leave your job. Make sure you add value for them vis a vis other investments they have made tangential to yours. Leverage your BigCo experience to help them with the pulse of your world.
- Broaden BigCo network – Message everyone. Tell them what you are planning. Create a communications plan for everyone you know. Schedule checkins with anyone ABOVE your grade. You can send the exact same message to 50 people individually. Every week or two, tell them something new, ask what’s up with them (target people per item 8 below). Keep it going while you are doing startup stuff. Send them cool startup details that make them jealous of your world. Keep your tentacles attached to BigCos…they can do the paycheck thing.
- Kids – Don’t do a startup if your kids are young. Don’t be an absentee parent. Mine were older (14 & 17) and I still felt guilty missing events. You have to commit every non-family waking hour to your company. I didn’t, it showed.
- College fund – Make sure your college fund or 529 can cover 3 years of college; fully loaded (books, tech, fees, travel). This was the one thing I got right. I admit, there was a lot of luck with my particular scenario, but it still made all the difference in making sure that I had school covered and that wasn’t an issue. Note: Luck for me = skill for the girls.
- Retirement – I don’t care how gung-ho you are (like I was), your retirement has to be solid. Don’t liquidate your 401k like I did. No matter how many billions you may think your exit event will yield, it’s not worth it.
- Living money – Have life expenses banked and ready. Don’t count on a funding event for your salary. You have to live. It is going to take 24 months to get a term sheet, if you even get one.
- Exit Strategy – Have a metric based exit strategy. Run out of money, time limit, number of customers, revenue, burn…whatever it is, set a mark and stick to it. That way you limit your financial exposure.
- Backup Plan – Most important part. Create a target list of companies and learn their products cold. Extend your network into those companies, start cultivating. Schedule meetings. Buy coffee. As you get close to the mark in point 7 above, start the plan. Change the tone of your contacts with your network. Start talking about what you learned. How it made you better. What you can share. You need to be ready with your resume the second you close the doors on your company.
I’m sure other failed founders have their own advice. This is mine. I truly hope you fair better than I did.







