A lot of folks regularly ask me this question so I’m going to blog about it. It seems weirdly narcissistic to think anyone would be interested in my finances but let’s give it a go.

My last paycheck was in June 2011. I quit to start a startup, or build a company, or something. I didn’t have much of a plan or much in the savings account.

I also don’t buy into the mythology that founders of meaningful companies need to spend years living in their parents’ basement and eating ramen noodles. My folks live in Florida so they don’t have a basement. And they wouldn’t let me live in it even if they had one. And I wouldn’t live there even if they let me. I wanted to become an entrepreneur and live on my owns without sacrificing my quality of life.

In those three unemployed years I’ve lived a pretty good life. I’ve lived in Manhattan, Brooklyn and Washington DC. I spent more than a month each in San Francisco, Barcelona, Buenos Aires, Cusco, Thailand and Bali. I spent more than a year homeless, traveling out of a backpack and working in coffee shops around the world.

I also had several close calls, ran up some credit card debt and spent a few sleepless nights googling personal bankruptcy. It’s been a wild ride.

So, first I’m going to list the various ways I scraped together money, then I’ll close with a few tough lessons learned.

Independent Consulting

My last job was at a consulting company advising cleantech investors and cleantech companies. While I was there it wasn’t crazy to book a six week project, where I did nearly all the work, for $75,000 – 150,000. Meanwhile over those six weeks I was paid maybe ten or twelve thousand dollars in salary and doing a lot of other work. Like many of my colleagues, I thought surely, there must be way to do this on my own. Bringing in just 50% or less of that amount would be a huge raise and I’d be able to operate on my own terms. So, after I quit my job, I reached out to companies for private consulting gigs. Here’s what I found out.

It’s totally true that you can split the difference and make (nominally) a lot more money. The first gig I booked was for a month or so of work for over $20,000. On an annual basis it was about $270,000, not too shabby even in NYC. But the sheen of independent consulting faded quickly. As a solo consultant you face a lot of tribulations that rapidly erode that shiny dollar per hour figure. Accounting is a nightmare, I spent hours tracking down invoices that were weeks or months past due. As a small consultant, clients feel entitled to bully you around constantly expanding the previously agreed, fixed-price scope, pushing back on hours and in general just making your life pretty shitty even without intentionally being jerks. This type of work is decent as a bridge to somewhere else but I got tired of it very quickly. It did however allow me to start earning some side income immediately after losing my paycheck, which was valuable.

I was working a lot with cleantech projects and was often offered success-based contracts, with big fees if I closed an acquisition, financing, or won a bidding process. I signed contracts with the possibility of earning over $250k over the course of a few months. I actually delivered about $75k worth of successes but my total take home was zero. Big fat waste of time and I would caution strongly against these “opportunities.”

The switch to software freelancing/consulting

The reason I quit my job was to build a startup that made educating homeowners about their rooftop solar insanely easy with software. I had no background in software, but I knew that I would need to learn enough to be dangerous, even though my initial plan was to hire or recruit software developers for equity (some of you are laughing at me already. Yes, I’ve since learned my lesson).

So in late 2011 I was devoting a decent amount of my time to learning to code. I was making steady progress when I had a realization. There was then, and remains now, a huge demand for software development. Instead of paying to learn to code, I thought I could big for freelance jobs, that I didn’t know how to do, and get paid to learn. So I went to freelancing sites like odesk.com and elance.com and created a profile. I barely had a portfolio (just some wordpress sites I made for myself and friends for free) and had zero credibility. So I made it a numbers game. I setup a workflow, with pre-written templates and automation that allowed me to apply for tons of small web development gigs.

Eventually I started to get some small $200 or $500 contracts here and there. Once I got a gig I would dive into the topic, reading every blog post and ebook I could and massively over deliver, winning both a happy client and a ton of knowledge in the process. By 2012 I was able to consistently get small jobs at a decent per hour rate. I worked very little, 10-20 hours a month and the net amount put me well below the poverty rate for the full year. But it was something.

In contrast to the strategic consulting I was doing in cleantech, software consulting is much lower stress. The client says “I want my website to X”, you do the work and show them “Look, your website now does X” and you get paid without much fuss. I’m not trying to make a broader point about the long-term benefits of different types of consulting. But if your goal is just to make some short-term cash, look for consulting opportunities where the deliverable is extremely concrete and success is very well-defined.

Geo-arbitrage is a bootstrapper’s best friend

I quickly realized that bootstrapping my business in New York City just didn’t make a lot of sense. Yes there are tremendous networking opportunities, but in the early days it’s mostly you on your laptop in a coffee shop building things, which you can do equally well anywhere in the world without NYC’s insanely high cost of living. I think NYC is an amazing place to build a funded startup, but if you’re on your own you should do what I did in early 2012 and run! I put all my stuff in storage and went full nomad, with just a backpack and laptop. I initially went to Spain for a few months but quickly headed to Latin America (Argentina and Peru). Compared to some big cities, traveling and living in hostels and Airbnb can still be a big savings. One month in Peru my total cost of accommodation was $180, about 10% of typical NYC/SF rent.

Combining the very small income from software consulting and my much lower cost of living I was able to squeak by through most of 2012. The details are for another blog post but 2012 was mostly a year of educational failures for me with three successive abortive attempts at launching my startup and three return trips to the drawing board. If I had not cut my costs to the bone I would certainly have been forced into getting a job by the end of that year.

I’ve used this kind of geographic arbitrage several times and it’s a great escape hatch in a cashflow crunch and good reason to stay away from long-term leases that you can’t easily sub-lease.

Storemapper: my tiny software business

Throughout this whole period I carved out some of my time for side projects. This was probably the smartest thing I did and it saved my butt several times. Sometimes collaborating with friends and sometimes on my own, I launched several small products. Almost all of them were failures but one of them, Storemapper, survived. I’ve detailed Storemapper extensively here where you can see that I launched it in late 2012. At first it was just a tiny trickle of subscription income. By mid-2013, when I moved back to NYC, it made enough roughly cover my Brooklyn rent. The whole time I was back in the city I was running my personal finances very close to the edge and at one point I completely messed up the accounting. I literally had like $300 in the checking account and rent was due in a week. At that point most Storemapper customers were paying me $5-9/month so I quickly hacked up a solution where they could switch to annual billing for $99/year and emailed all the customers. Fortunately about 15 of them took me up on the offer and I made enough money to pay rent and buy myself a small victory beer. These days Storemapper generates about $80,000 in annual subscriptions, which is freaking awesome. This whole story would look very different if I had not found this source of subscription revenue through trial and error. By very different I mean that I probably would’ve been bankrupt. So, hard to overstate the importance of side-projects.

Friends are awesome

I would be massively remiss here if I didn’t mention the help of friends. I was never one for asking for favors until I decided to try to build a company, and a life, on my own. You get over that pretty quickly. Friends of mine have come through big time in the last few years, letting me crash couches and housesit for much longer than reasonable lengths of time. They know who they are and they are awesome.

Credit Cards are useful

Saving the most controversial for last, yes, during the last 3.5 years of trying to build several different companies I racked up a five figure credit card bill. Right before I quit my job I signed up for a ton of credit cards and loading up on both ready to access capital and bonus frequent flyer miles (almost all of the traveling from above I did using miles for basically free).

I’m honestly not sure where I stand on credit cards. For sure I could not have gotten access to that much capital through a traditional loan of any sort. As I started this journey I was convinced that it would be at least as educational (if not radically more so) as an MBA. At its peak my credit card debt was less than one-fifth the cost of a top tier MBA so I genuinely think it was a good wager in the long run. That’s still a lot of debt though. In the short run it’s much more stressful than nice subsidized and negotiable student loans.

I think it’s a huge shame that it is so easy to get a loan for a $100,000 grad school with pretty dubious value and nearly impossible to get $20,000 to cover living expenses while you build, learn and experiment. But those are the facts. Without access to that credit I certainly would have had to quit and get a job. It worked out for me and I’m on track to nuke all my debt by early next year, but it’s also a risky and stressful move.

Lessons learned

I’m in a good mood right now, just finishing up three weeks in Iceland. I saw some great Northern Lights last night and they’re supposed to be better tonight. So I’m concerned this blog post paints too rosy a picture. I quit my job with very little savings and no real plan on how I would make nearly enough to cover my cost of living. I plowed my little savings into learning things and failed spectacularly for a long time at launching my company(ies). There multiple times where I was very seriously googling personal bankruptcy and several times where I only barely was able to make ends meet. I feel now like I’ve only just barely made it out of the gauntlet. There’s still some credit card debt to deal with and my taxes where a complete clusterfuck that I’m only just now getting in order. But, here are some key things I feel I have learned:

1. Keeping overhead low is essential. The biggest mistake I made by far was moving back to NYC before I had any meaningful income. Every month you live in that city you need to spend like five grand. It’s stressful, it limits your options and kills your creativity.
2. Maximize flexibility. I have never signed a lease in my life. I don’t have a car, a dog or a cell phone contract.
3. Ask for help. When you do some stupid and crazy, you’ll be surprised how much your friends want to see you succeed.

There are more lessons learned but this post is getting too long. I’ll think harder on this and write another post.