Bootstrapping in the City: The Long Lost Days


bootstrapping nyc

If you’re at all connected to the entrepreneurial scene, you should read Alice Warwick’s article in Wired on how it’s “dangerous to hero-worship entrepreneurs.” It’s a great opinion piece and while I don’t agree with many of her points, including the idea that tech entrepreneurs’ pursuits to change the world are disingenuous, it definitely creates for some lively debate (as the 352 comment thread is a testament to).

One point I cannot disagree with is how misguided it can be to idolize entrepreneurs. The truth is starting your own business is not as glamorous as it’s made out to be. But it makes sense that we idolize these stories of rags to riches, like Andrew Carnegie and Horatio Alger and more modern ones like Oprah and Jim Carrey. It’s the epitome of the American story and values. But it’s the process of getting from point A to A1 that escapes the popular narrative. In fact, when I’m asked how I started my company, the questions are never about the middle chapters– the stories of the uncredited contributors, the starts and stops, the failures, and the struggle. And even if I were to mention it, would it ever get any air-time? Well, here’s a quick recap of some lessons I learned that helped me survive the bootstrap phase. A phase I know, perhaps all too well, on how to survive and to succeed at.

“Lesson 1: Terrified? Good, keep going.

I started my company during a bit of a life crisis. I was moving out on my own with less than a month’s notice, jobless, dwindling bank account and the nail in the coffin was my obsession with a big idea. I was facing an uphill battle and the deck was certainly stacked against my favor. I was terrified but instead of turning back, I kept going. Had I not kept going, I would not have built priceless memories with an entirely new social group, or found the initial program to help kick start the business, or to experience the ultimate life lesson that proceeding into the unknown can be incredibly liberating and life-changing.

“Lesson 2: Say goodbye to comfort. 

The next focus was eliminating and reducing all extraneous expenses. Staying financially lean was the lifeblood for my idea, the company and my survival! While this may be an obvious lesson, the devil is in the details and it’s all about the how. I went from a mid-town luxury condo to living with roommates in Fort Greene off the G train. Prior to that, I had sworn I would never live off the G line and thought anyone who did so must be clinically insane. Nothing is absolute and as fate would have it, I ended up signing a lease off the G train, with roommates for $850/month. For those of you in NYC, you know just what a steal that is. And starting the day of my move-in, I waved goodbye to late-night taxi rides, delicious lattes, $15 cocktails and eating at the next critics pick hot spot.  You will be surprised just how lean you can stay while still enjoying life in the city. Here are some gems I found along the way:

  • Entire dinner menus that you can cook from dollar store ingredients! While I don’t recommend doing this every night, this can be the make or break on getting that rent in on time.
  • How to survive in NYC on 99 cents
  • I recommend trying to find roommates through you own networks first, but if that fails then there’s always: Roomates, Livewithus, Crashpad and Livelovely

Not surprisingly, there are a ton of “free” lists for things in NYC:

  • Timeout’s list of free events, date ideas, tours, art
  • An updated list of weekly free events (mostly music) by the City of New York
  • Strange but interesting mix of free things from meditation and yoga to beer crawls by Buzzfeed

“Lesson 3: Be Scrappy.

And so there I was, with my new apartment and no money to furnish it. And as an adult, I refused to live as if I were still a poor college student. I became boss of the free craigslist listings and ended up furnishing everything for FREE. That’s right, zero, zilch, nada was spent and I had a pretty incredible place (see exhibit A). I did the same thing for the company by finding free workspace (that also had free coffee, +1), to pitching partners and finding collaborators to help build the initial proof of concept out. Here are some of the resources I couldn’t go without:

  • From outfitting your home to your office space, Jesse McKinley from the New York Times does an incredibly detailed job on breaking down how to get it done for a mere few dollars.

Affordable office space in NYC:

  • Hive at 55: Great co-working space where you can go just for the day or rent out dedicated space. Free coffee too, which is never a bad thing :]
  • Projective Spaces: Great founders and very cool spaces. They also host a lot of events, so it’s an easy way to network without leaving your office. Only downside is that it can get a bit loud sometimes, but nothing that a good pair of headphones can’t fix.
  • WeWork: I’ve never worked here myself, but know a lot of people who live and die by it. Rumor is they not only have free coffee but delicious flavored water?! Lots of locations in the city, so take your pick.

Some of my favorite and free productivity tools that you’ll soon get addicted to:

  • Evernote for note taking/organizing
  • Freshbooks to simplify accounting
  • Dropbox for file management and remote access
  • Insightly for CRM and project management

Learn, without the huge price tag:

  • Skillcrush: Basic coding boot camp. Great for first timers and comes with 1:1 support and mentorship.
  • Code Academy: Interactive coding model with a huge network of users.
  • General Assembly: Not into coding? Check out GA’s options that range from business, economics, management, design and art courses.

Whenever I meet new entrepreneurs, the fastest way to bond is over these bootstrap stories, tips and tricks. I just wish we shared them more vocally with everyone else. These vignettes humanize the narrative and reflect what it’s really like to build something out of nothing. It’s not a story of weakness; it’s one of vulnerability and truth which feels like courage. And hey, it doesn’t hurt to have the street cred–“Oh, living on nothing and building a company? Sure I’ve done that.”]

Have a good war story or going through it now? Drop me a line or comment below, I’d love to hear about it!

Reprinted by permission.

Image credit: CC by JMazzolaa

About the author: Lily Liu

Lily is the co-founder of PublicStuff. Her inspiration to start PublicStuff came from direct experience working in government, including Mayor Bloomberg’s Special Project & Analytics team, the City of Long Beach, CA and TSA. Lily was recently named one of Forbes’ 30 under 30′, received her Master of Science from Carnegie Mellon University, is a self-proclaimed adrenaline junkie, and a lover of the arts.

You are seconds away from signing up for the hottest list in New York Tech!

Join the millions and keep up with the stories shaping entrepreneurship. Sign up today.