Highlights and lowlights from the first 3 months of a new consulting business

by Michael Bernstein on January 26, 2017

A little more than 3 months ago, I announced to “the world” that I had left my job and was looking to start my own thing. As usual, I did that via Twitter:

Since then, I’ve…actually survived! Not bad, right? Actually, things have been going pretty well, and I’ve learned a few important lessons. I thought I’d share those in the form of some highlights (and some accompanying lowlights), in the spirit of all the folks who helped me when I was starting out.

Finding a partner

I started out alone, and while that was great, things have been going considerably smoother since I found a partner in Brian Doll. The slack that it allows me in my day to day life is huge, and I know that because Brian is someone I can trust implicitly to be motivated to do amazing work, I know that we’ll always be representing like we should. I can have faith in our services because I know that everyone involved really, really cares.

There were definitely some low moments when I was pretty sure that there was no chance that I was going to be able to pull this off, and I got desperate enough to pretty much give up and did some job interviews. I felt like I would be considerably worse off and unhappy in any of those jobs, though, which definitely helped motivate me.

Keeping it small

When Brian and I partnered up, one of the reasons we both knew that we would feel comfortable devoting at least 5 years to this business was that we both wanted to keep it small. We have constrained ourselves numerous times in terms of what we invest our money and energy into based on this simple principle.

In the time leading up to forming Reify with Brian, there were times when I had conversations with other folks about starting projects. What I’ve found is that if you ask someone “Do you want to keep this small?” and they respond with “Yes, unless the opportunity presents itself…” then they may still be the partner for you…but they don’t really want to keep it small. Making decisions that assume your business will always consist of two full-time people is challenging. For us, so far, its been worth it.

Nailing the pitch…and missing the mark

Some of the most cringeworthy moments in the last few months have been when I just haven’t been able to communicate what the hell it is that I’m trying to sell someone. I’ve gotten some really busy, talented, well-connected people on the phone, and tried to PITCH THEM EVERYTHING. The best way to sell your services, as a consultant, is to be confident and clear about precisely how you think your expertise will help a potential client solve an acute problem they have right now.

A good example of this is when I almost completely blew a deal with a VC who was at the time the acting CEO of a startup we were pitching. I tried to sell this person absolutely every service under the sun, without seeming interesting or compelling about any of them. Right before I was about to give up, it occurred to me: I haven’t actually said anything concrete. I mentioned that we had recently done some work with a startup to help them get ready for a conference they were sponsoring. DING The client snapped to, mentioned how his company was going, and asked me “How much for a day of that service? We want to buy that right away.”

Talking to absolutely everyone

The best part, by far, of launching this consulting business has been the conversations I’ve had with the talented, dedicated, typically very sleep-deprived, founders and executives of companies that do something that is very important to me. Making great tools for software developers is an interest of mine that runs deeply: I use these tools every day, I’ve spent time making and selling them, and now I spend even more time thinking about them.

I’m inspired by the quests of everyone who is involved: people who are making small businesses for themselves, people who are dreaming huge, and everything in between. I’ve never been an inventor as much as an enabler of inventors, so this, for me, has been a huge thrill.

Finding joy in the mundane

Hiring a lawyer. Making contracts. Hiring an accountant. Choosing software. Sharing calendars. All of the little steps, brick by brick that build our business, are easy for me to find joy in. I like making things more efficient when I can, or realizing that I don’t always have to, because hey, we’re small.

The community of hustlers who make it on their own are a proud and sometimes prickly bunch, but it’s been amazing to join their ranks. They’ve welcomed us with open arms, and I think that this is something that we all share: we don’t mind doing the dirt, because at the end of the day, we own the farm.

Being super scared

At times, this has been very frightening. Knowing that we’re putting everything on the line, riding on our reputations and ability to sell, on our own desire to keep it going, can be challenging. Waking up knowing that you’re the one in charge of how you spend your time is thrilling, but can also be defeating if you don’t keep on top of it.

When client projects don’t work out, when checks don’t come on time, when you’re not sure if you’re making the right decision about taxes, when you can’t come up with a good idea for your writing assignment, when you can’t and can’t and can’t … remember that you can. Reminding myself, constantly, that I’m confident, qualified, and engaged really helps. On some Stuart Smalley shit, for real.

…and lots more to come.

One big highlight of this whole affair has been realizing that our business relies, in a sense, on our optimism. This is huge, for us, because, well, we’ve got plenty of that to go around. We know we have to be optimistic about the things we haven’t yet accomplished, and we know that if we keep our sights set on the big goals, that we’ll be that much closer to achieving them.

Having big lists of things we’d like to accomplish has been an amazing motivator. We know that we have books to write, videos to record, courses to teach, clients to work with, deals to make, software to write, and more. Everything we cross off, and everything we add, we do for ourselves.


Thanks for tuning in to our story so far — let us know if you have questions, or want to share experiences, or, as usual, to tell us that we’re full of shit. We’d love to hear from you!