How Bootstrappers Can Compete Against Funded Startups and Get Customers

Written by on Nov 13 2013
funded against bootstrapping

LessAccounting is a product Steve and I started working on in late 2006. Over the past seven years, we’ve seen many vc funded companies enter the market, and many come and go. Some begin with “only” $3 million in funding, some with $50 million or even $230 million in funding. Then you have us, a handful of awesome people, who bootstrapped by clawing and scratching our way in a market surrounded by giants.

Because of our profitablity we’re the cockroach of the accounting software industry… because we cannot be killed.

So how do you compete with vc funded companies with deep pockets and tons of resources?

First realize this, you cannot outspend them.

  • You don’t have $40,000+ to sponsor the big name industry events/tradeshows/conferences like they do. You can’t afford to buy a booth, install flat screen TVs and hire marketing staff to travel to industry tradeshows and shake hands.
  • Having no extra piles of money around means you can’t hire more people than they can. Your funded competition will be hiring anyone with a heartbeat, and the managers to watch over them. You cannot afford to hire anyone.
  • When you do hire, you can’t afford to pay the salaries the giants offer.
  • They’ll set up offices in large tech hubs, and hire a chef for their beautiful offices. You might not be able to afford to live in a city where rent is thousands of dollars per month.

Being Small, Nimble and Yourself is Your Only Advantage

Focus on small events

Large companies focus on “big plays,” which are events that have huge attendance levels. These events are “worth their time” and expenses to sponsor and attend. When your competition has this “view” on marketing, it leaves many small events with 10 to 200 people up for grabs.

So while you might not have $40,000 to spend on one event, do you have $1,000 to sponsor 10 small events/gatherings? We’ve sent cupcakes to many accountant meetups in the past few months. Most event hosts will allow you buy them pizza, beer or cupcakes at just the cost of the goodies. Being a small event, they’re just happy to have anyone sponsor. Ask for the opportunity to give a 5-minute demo before the meeting starts using

Here’s how we sponsored an event with American Airlines for $500.

Do Things They Simply Can’t Do

Larger companies have approval processes for design and copywriting. These processes protect them from possible legal issues by trying to avoid offending anyone. Your website copy, design or even blog posts do not need to be approved by lawyers. You can be bold, or even irreverent, but be yourself.

Doing things larger companies cannot might include throwing a crazy conference for entrepreneurs, might be weird stickers or even an irreverent product tagline. Find things large funded company can’t do, or simply are too small to focus on.

You might find a podcast about Star Wars to sponsor.

Be an Advocate for Other “Smalls”

I love being the company that promotes others. Even on our login page, we promote other artists to our customers. When I blog I love to talk about other people in similar situations, awesome people duking it out for business, being themselves and having an opinion.

Talk About Being Small

Businesses that have an opinion and share it gain popularity. But rarely does anyone talk about being “small,” having a small company and struggling, and the pressures and stress from it. Realize your industry peers and your potential customers love the underdog. So tell your story. Tell it over and over, and tell it in whatever you do.

Side Note: In case you don’t know, LessAccounting is a bootstrapped product that was started in 2006 by two fat, handsome gents. Our product is simple and requires no bookkeeping knowledge to use. Today only, if you sign up for LessAccounting, I’ll personally drive to your location and give you a hug. Would a large funded company do that? Probably not.


Being a small, bootstrapped company means you cannot follow a larger company’s path. Your only advantage is being small. Continually ask yourself, “what advantages does being small and self-funded give me?”

Also read David’s article on “Constraints Breed Breakthrough Creativity”.


Hi I'm Allan,

I wrote the article you're reading... I'm one of the co-founders of LessEverything. I love my family more than breathing and I love creating videos about our family adventures.

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