30 Founders in 30 Days

Earlier this year I was asked to perform a series of short advisory sessions with a group of founders. The founders ran the gamut from just putting their vision together, to working through the first year post-launch, to being years in and ready for a pivot. They ranged in industries from UX design, to new wellness technology, to maple syrup (who doesn’t love maple syrup?). Thirty founders in and I’ve learned a ton about where founders struggle and some of the simple fixes that make their lives easier.

When Sophia Amoruso asked me if I would be interested in conducting thirty-minute, “ask me anything” calls with some of her students in the next round of Business Class I had quite a few emotions. My first reaction was verbal paralysis, but internally I was thinking: Is this really happening to me? Can I do this? Should I do this? Is this really my life now? After sleeping on it, speaking to a few people whose opinions I deeply value, and becoming aware of my own issues that were holding me back, I said yes. Yes yes yes! Now halfway into this adventure, I’ve already learned a huge amount about what founders need and how we as lawyers and advisors can be even more helpful to them. Below are some of the issues I’ve heard most frequently and, in case you can relate on some of these, the advice I’m giving.

PROBLEM: Lawyers are scary. SOLUTION: First, true! They often use a lot of jargon and have a tendency to talk down to people, but not all lawyers are created equal[ly scary]. If you think you might need to talk to an attorney, ask your peers for a recommendation. Your peers are small business owners like you and they will understand the kind of attorney who is helpful versus one who makes you feel dumb and just hands you a stack of documents you don’t understand.

PROBLEM: I need cash. SOLUTION: There are many, many ways to finance a new business: your own cash, money from friends and family, small business loans, grants, raising capital from angel investors or venture capitalists, and tailored financing from private credit firms. This is not to say that all of these options will be available to every company. But don’t feel like it has to be bootstrapping or raising millions from VCs. There are plenty of options in between.

PROBLEM: Is this even a good idea? SOLUTION: This isn't really a lawyer question but I hear it all the time. This is the self-doubt that visits every entrepreneur, creative, and anyone else who is out on a ledge doing their own thing. Am I crazy? Will anyone ever buy this? Do you think I’m an idiot? Am I an idiot?!?! Perhaps the single most important thing you can do at any point in your company’s development (even in pre-development) is to speak to users. Why don't we do it? For the same reason we don’t just ask someone if they like us: because we’re afraid of what they might say. But you need to know. If you’re selling something, you need to find out if it’s something people want. In fourth grade Ben Cates dropped a note in my lap that said, “Do you like me?” with boxes for YES or NO. Not one to be told what my options are, I responded with a lengthy explanation of the conditions under which I would say yes. Needless to say, things didn’t work out. Be more like Ben Cates and hope for users like me who will tell you what’s what.

PROBLEM: I’m afraid I need a lawyer but I’m not sure. SOLUTION: Sometimes you really don’t need a lawyer, or at least not one you pay for. There are plenty of free resources out there to extend beyond a Google search. Top resource: your peers. They’ve already gone through it, so use them. Second best resource: government services for small businesses. Everyone from the Small Business Administration to state-run Departments of State to city-run Chambers of Commerce exist primarily to support you and make you a success and, for the most part, for free! They might even have lawyers you can speak with.

This has also been an important and at times painful learning experience for me as well. It’s hard work to be put on the spot, with no background, and a different industry and development stage each time I get on the phone, and then try to sort through it all and make sure they get the information they most need. When you work at a big firm, to some extent, things are spoon fed to you. By and large you work with other lawyers inside large corporations. You get used to answering specific legal questions that have already been formulated for you by other, often incredibly experienced and fantastic, lawyers. This may be why many founders, when they first speak with lawyers, feel like they need to know the questions before they even arrive, because that’s how most of us “grow up” at firms. 

How do we get away from that and become more useful? I have to think the most important thing is being a good listener. As I recently told a truly impressive group of women at a dinner two weeks ago, I used to think my superpower was listening, but then I started reading You’re Not Listening by Kate Murphy and realized I still have plenty of room for improvement. Fortunately, my days are rife with opportunities to exercise this muscle. 

Finally, a quick thanks to Sophia and her team for inviting me to speak with your founders, and to each of you who have trusted me with your precious vision. 

--Jessie Gabriel