13 Habits of Successful Bootstrappers

Question: What are some habits that all successful bootstrappers have?

Question by: Morgan S.

Keep Calm and Carry On

"By definition, bootstrappers have a lot of responsibility and a lot on their plate; there are many variables being juggled at once. The best of the best keep an uncanny sense of calm amidst the surrounding chaos by keeping things in perspective. This way, they can execute on many important tasks without compromising their creativity, enthusiasm, and ability to inspire others."

- Kent Healy | Founder and CEO, The Uncommon Life

Never Stop Learning

"When you're bootstrapping a business, you need to wear many different hats, and that usually means learning some new skills. Because of this, bootstrappers are great at picking up new skill sets, teaching themselves how to do new things, and learning more about their line of business."

Know Yourself Well

"Do the homework to know yourself incredibly well: look back at past experiences, ask others close to you, take the StrengthsFinder 2.0 assessment. Have the confidence to know what you're naturally awesome at and the honesty to know what you're awful at. Then dedicate your time to the former and find amazing talent to take care of the latter."

- Scott Dinsmore | Founder & CEO, Live Your Legend
Make the Trade

"Many successful bootstrappers trade services to get what they need to build their business. Whether it's designing websites in exchange for legal advice or an in-kind sponsorship in exchange for free accounting, bootstrappers know how to get creative when trading services for what they need."

- Tim Jahn | Co-Founder, matchist

Negotiate Often

"Almost everything is negotiable. As a bootstrapped startup, you have to make a habit of always asking for a better deal, free bonuses, additional "extras" thrown in, longer payment terms and more. Read a couple of books on negotiation such as "Getting To Yes: Negotiating Agreement Without Giving In"—they'll pay for themselves a hundred times over."

- Matt Mickiewicz | CEO & Co-Founder, Hired

Wake Up Early

"As a budding entrepreneur that wears many hats, there are simply not enough hours in the day to get everything done. Especially when you're bootstrapping and finances are tight, time is vitally important. Most successful entrepreneurs wake up early in the morning with excitement and dedication."

- Logan Lenz | Founder / President, Endagon

Keep Your Day Job

"In the early days of bootstrapping, you're going to be obsessed with cash flow. So rather than worry about paying for your bills, keep your day job and incubate your startup on the side. Once your startup is cash-flow positive with a killer growth plan, then you can confidently quit your job and go full-time on your venture."

- Eric Bahn | Advisor, Webflow

Eliminate Unnecessary Expenses

"All successful bootstrappers know how to spend their money. Bootstrappers are not necessarily cheap. If it's a good investment, they will shell out as much cash as they can, but if they cannot justify the cost, why would anyone pay for it?"

- Danny Wong | Co-Founder, Advisor and Lead Evangelist, Blank Label
Commit Long Term

"To keep costs low in the early and fragile startup phase, negotiate with vendors for longer contracts that have lower monthly payments. This will help maximize your profits during startup stage so that you can invest and grow your revenues. Once you get to a better financial position, you can renegotiate your contracts."


Stash the Cash

"When bootstrapping, it's important to hold on to your cash (as much of it as you can) for as long as you can. Just because you land a client/sponsor doesn't mean you necessarily should fly to Vegas and celebrate. Focus on building your business, being lean and continue to build up cash for as long as you can. Cash is, and always will be, king."

- Jason Headsetsdotcom | Official T-Shirt Wearer, IWearYourShirt.com

Invest Wisely

"One of the biggest mistakes you can make is spending your initial cash infusions on things that don't help create more cash infusions. Invest in things like coaching, website improvements, and things that will help your bottom line in the long run."

- Srinivas Rao | Co-Founder, BlogcastFM
Find Solutions, Not Excuses

"Successful bootstrappers look for solutions, not for people to blame. Failing business owners rush to find an explanation for their failure whereas bootstrappers think logically, laterally and intently to figure out why it’s happening. Once the reason is discovered, they work feverishly to correct their course. Failing business owners instead succumb to excuses."

Play More StarCraft!

"StarCraft has taught me many lessons related to entrepreneurship—in particular, effective time and attention management. A good StarCraft leader must balance micromanaging units with high level strategy, all while delegating tasks, working quickly and maximizing the use of limited resources. These skills are very important when bootstrapping, and StarCraft is a great way to get practice!"

The Young Entrepreneur Council (YEC) is an invite-only nonprofit organization comprised of the world's most promising young entrepreneurs. The YEC recently published #FixYoungAmerica: How to Rebuild Our Economy and Put Young Americans Back to Work (for Good), a book of 30+ proven solutions to help end youth unemployment.

About YEC

The Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world's most promising young entrepreneurs. In partnership with Citi, YEC recently launched StartupCollective, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses.

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