About

Ryan Crownholm

Ryan Crownholm is a serial founder & entrepreneur, mentor, investor, and U.S. veteran. With grassroots in construction, formerly a Class A General Engineering Contractor. He has an exceptional track record of developing business models that deliver immediate and sustainable returns and is able to help business owners to identify promising business concepts, build high-performing teams, and create winning plans for attracting customers and maintaining bottom-line profitability. An accomplished serial entrepreneur, Crownholm mentors a variety of individuals, including entrepreneurs, CEOs, veterans, and both currently and formerly incarcerated individuals. His mission is to practice insubordinate entrepreneurship and to change the current landscape for small business owners and entrepreneurs.  

Crownholm currently runs several businesses, which allow his expertise as a founder to shine through with his mission of helping his community thrive. He is the president and founder of Crown Capital Adventures Inc., founded in 2014. He co-founded the construction technology solution, Dirtmatch.com, which is a marketplace where contractors, homeowners, and companies connect to exchange fill dirt.​​ Mysiteplan.com, founded in 2015, is a website that allows people to purchase informal maps for their property drawn from preexisting information and images. The company helps simplify the permitting process for simple projects that require non-certified site plans. As a consultant, Crownholm helps CEOs step back from their company and manage by metrics.

In defense of entrepreneurship, Crownholm has partnered with the Institute for Justice and is currently in a legal battle with the state of California over CA's licensing requirements. He is fighting against unjust laws that hamper innovation and hurt consumers. 

Crownholm was an early adopter of blockchain technology and has been involved in several high-profile crypto and NFT projects, including partnering with Western NFT Partners LLC and serving as an advisor at The Crypto Company (CRCW), and the Blockchain Training Alliance. In April 2022, he collaborated with ​​former NASA Astronaut & retired US Navy Captain Scott Kelly to raise $500K in just 6 hours using Artistic NFTs. The funds were raised to aid Ukraine at the outset of the Russian invasion.

Crownholm started his professional career serving in the U.S. military from 1996 to 1999 where he served in Germany and Bosnia as a part of the NATO operation joint endeavor. He had joined with the purpose of receiving money for higher education. While studying at college, he started his first business in 2000 which was a hauling and junk removal company. By the time he graduated, he had gone from 1 employee and truck to 20 employees and 10 trucks, achieving $1MM in sales. He grew that company into a demolition, excavation, and trucking company which became the largest swimming pool removal contractor in America. Crownholm started a property preservation company in 2007 which fixed up homes for banks who foreclosed on the properties. In 2008, Crownholm opened free recycling centers and held free recycling events across the Bay Area, his company “Dump My TV” recycled 1M lbs a year of electronics and appliances, diverting them from landfills, becoming a tremendous profit center while providing jobs to underserved communities. Crownholm founded an online construction drafting company in 2013, and went on to the construction technology solution, Dirtmatch.com, in 2016, which he still owns and runs. 

Crownholm holds a BA in economics and business administration from St. Mary’s College of California. Prior to that he studied different types of business at Diablo Valley College, the City College of Chicago’s U.S. army extension, and the University of Maryland’s Bosnia extension which consisted of him and 4 others huddled around a heater in a tent in Bosnia learning about business. 

Crownholm has become a mentor to a variety of communities, including veterans, currently and formerly incarcerated populations, CEOs, and more. He wants to share his 20+ years of mistakes, successes, and wisdom that has accumulated and allow others to benefit from his entrepreneurial journey. He aims to change the way that founders interact with funding and the culture around fundraising, how entrepreneurs play by governmental regulations that have no basis, how communities view and treat veterans and incarcerated peoples, and to evolve the current landscape for small business owners and entrepreneurs through insubordinate entrepreneurship. He volunteers for Defy Ventures and serves on the board for Equip Our Kids, a national nonprofit campaign raising needed awareness about and support for EQ life skills, especially among parents and children.

Crownholm is a member of organizations such as Genius Network, Summit, METal, and the Boulder Investment Group, The Syndicate. He has been featured in publications such as VICE, the OC Register, Bay Area Masterminds, and podcasts such as Hooked on Startups and Break Free: The Best Business Podcast.

The Hustle Trap

A How-To Guide for Doing Less + Making More with Your Business

Sometimes it takes a radical event to change your life. After an almost deadly work accident, Ryan Crownholm faced a difficult truth about his business: without him, he felt failure was imminent. Change was no longer a choice. His—and his company’s—survival depended on it. In The Hustle Trap, Ryan shares the principles that helped him build a passive seven-figure income while creating more free time to focus on what matters most. This is a comprehensive guide for creating a sustainable business and supercharging your cash flow. Through Ryan’s personal stories and illuminating examples from more than two decades as an entrepreneur across many industries, you’ll learn how to implement key principles for transformation and peace of mind. Escape the hustle trap with this must-read for entrepreneurs wanting to work less, make more, and find freedom for a joy-filled life.

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