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Don’t Ever Stop Bootstrapping: The Most Inspiring Thing You’ll Do as an Entrepreneur

My point is, always have your ‘skin in the game.’ Keep your expenses down. Care about your costs. Don’t rest on your laurels…

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1 – Bootstrapping

Don’t ever stop bootstrapping. Don’t.

My point is, always have your ‘skin in the game.’ Keep your expenses down. Care about your costs. Don’t rest on your laurels… and keep caring about how that dollar is spent on Day One as Day 2,555 (7 years which is the average start-up mode). Why would you ever stop caring about hard earned dollars?

That doesn’t mean you can’t think big. Garner more resources. Attain significant investments from major investors. But always care. Don’t lose your “bootstrap caring.” Every one has put forth some serious investment to make their money. Respect their money as you do your own.

2 – Family and Friends Close

Keep those close supporters for family and friends — close. It’s not just financial support. It’s ‘history’ support, emotional support, track-record support, ‘wisdom’ support of someone having seen you build something from scratch — and maintain it. Keep those people who respect you very near with great, great ongoing appreciation. For some years after that initial investment, it may be more that they continue to be a sounding board or a positive cheerleader as you make advancements. As you grow your business, they might jump back in financially at a needed time. If you’ve kept them educated and inspired, they understand your need and will most likely help.

3 – Share, Incubate

Right now we’re in our 7th year and we are fortunate enough to share office space with Kapor Enterprises, founded by Mitch Kapor, the founder of Lotus Notes and Second Life. He and his wife provide an amazing space, where people of all diverse backgrounds of different races, economic levels, business, nonprofit, foundation, investments, reside. The environment is not an incubator; rather it is an entity that provides an extremely supportive and crossfunctional environment allowing entrepreneurs and more established leaders, the opportunity to succeed.

Incubation is an option. Shared office space to cut costs and increase camaraderie with another entrepreneur. Or you can even ask a larger company if they have extra room. The point is, get into an environment that will help you, and your team, succeed more rapidly.

Remember as an entrepreneur, you may not ‘see’ your environment. I didn’t when I was building UniversalGiving. I was in my home for 2 years with printed three-year budget and contingency budget scenarios all over my roommate’s living room. When I cofounded VolunteerMatch, I worked alone in a one room brick office with no windows. We entrepreneurs just want to get things done. We have a vision and we are stepping into that reality urgently. Who cares if there are no curtains, the rug doesn’t match, my bed isn’t made…? Or my favorite, it’s too taxing for me to think about clothes so I end up wearing the same thing two days in a row… We need to create!

So the point is… not everyone is like that. Your team may need a more supportive and inspiring environment. And, it’s good to treat yourself to that, too! At KEI, we have CEOs and foundation executives and program managers and nonprofit leaders… all of which make for rich discussions, new insights, helpful collaborations.

Let’s keep some of our entrepreneurial motives throughout the longevity of our organization. As entrepreneurs we can commit to caring about our resources and relationships well beyond startup mode.

Saluting entrepreneurs, Pamela

Thank you to Marty Zwilling, whose Forbes article “Top 10 Resources for Start-Ups” inspired this post.