Serial Entrepreneur

david douglas stone

I’ve built and scaled several early-stage ventures, worked for Fortune 500 organizations to launch multimillion-dollar initiatives, and repeatedly helped others achieve similar success.

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Interior of Orange Bike Brewery filled with guests

Interior of Orange Bike Brewing Company, where David is an investor. Orange Bike is Portland, Maine’s first dedicated gluten-free brewery, committed to making social, environmental, and financial impacts within the craft beer industry.

David Douglas Stone smiling and wearing a red scarf

about me

Since starting CashStar in 2007, acquired for $178MM in 2017, I have been thoroughly committed to advancing Maine’s startup ecosystem through board service, investing, advising, mentoring, and most importantly inspiring the next generation of entrepreneurs.

I’m driven by four core passions:

  1. Creating and building innovative companies that capitalize on emerging market shifts — my primary focus;
  2. Bringing transformative products and services to market that fundamentally shift customer behavior through hands-on advising and tech-enabled innovation;
  3. Applying strategic, intuitive, and unconventional ”recombinant” thinking, through a direct, values-forward leadership style; and
  4. Driving social impact by helping founders build companies that do well by doing good.
more about me

My Services

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advising

With over twenty years of successfully creating and building great companies, I’ve achieved cumulative exits in excess of $¼ billion and helped Fortune 500 companies and a host of early-stage ventures achieve more than $300 million in revenue.

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thought leadership

I am a market intuitive and innate strategic thinker, having developed and launched several new product and service categories, setting trends that have reshaped business and consumer behaviors.

icon of person at a podium

speaking

Known as an inspirational and unconventional speaker, I have been featured in leading publications and broadcast media and spoken at numerous events and conferences. I bring passion and conviction to topics and ideas that excite me.

icon of a globe with a gear inside, representing social impact

social impact

At a time when the world is shifting away from personal well-being, justice, and environmental sustainability, I am now more committed than ever to supporting businesses that directly address complex, high-impact social challenges.

Mark Twain

“Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did do. So throw off the bowlines, sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.”

Steve Jobs

“You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something: your gut, destiny, life, karma, whatever. This approach has never let me down, and has made all the difference in my life.”

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Jean-Jacques Rousseau

“To live is not to breathe but to act. It is to make use of our organs, our senses, our faculties, of all the parts of ourselves which give us the sentiment of our existence. The man who has lived the most is not he who has counted the most years but he who has most felt life.”