011: Taking on the big boys and winning, with Ryan Crownholm


This week I talk to Ryan Crownholm – a serial entrepreneur with a long and successful track record of moving into established, highly competitive industries and transforming them by introducing technology, branding and marketing.

1:24 – Digging into specialized niches to compete with large, established companies.

1:50 – Ryan’s first business, Hauling Pros, and how he identified the opportunity and grew organically.

3:35 – Deciding to be unemployable after leaving the military.

4:07 – How he found the funding for his business early on.

5:21 – How he knew this was an opportunity worth pursuing.

6:15 – Advice for recognizing opportunities and getting started.

7:26 – The value of starting small and growing organically rather than raising capital and starting big.

8:27 – Advice for entrepreneurs starting out a new business.

9:43 – Looking internally for business ideas rather than asking others what business to start.

10:27 – Ryan’s knack for developing businesses that solve problems for people, like his former business, DumpMyTV.com.

11:46 – Creating a business to solve a problem rather than creating a more complex problem, addressing little niches.

13:01 – Ryan’s path to starting IHateMyPool.com, finding a focus by examining market needs.

14:41 – Entering a market that’s set in its ways and then solving problems in a new way and experimenting.

15:14 – Developing new businesses from solving his own problems in the pool removal business, DirtMatch.com and MySitePlan.com.

17:33 – Should you do something you love or love what you do?

18:23 – Moving into mentoring and helping others to grow their own businesses through the lessons he learned the hard way.

19:43 – Focus more time on your business and less on fundraising.

20:24 – Getting one paying customer as a proof of concept before obsessing over the perfect product.

20:52 – Understanding growing a business before trying to bring on investors or a business partner.

22:32 – Dealing with regulations and governmental bodies.

23:21 – Being an entrepreneur vs. being a manager.

24:39 – Get started and update your products and processes as you go.

25:23 – What Ryan is most excited about right now.

26:47 – Ryan’s guidance for new entrepreneurs.

28:19 – Ryan’s book recommendations: “Guerilla Marketing” by Jay Conrad Levinson and “The 4-Hour Workweek” by Tim Ferriss.

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