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Meet the Advisors at Cultivate

April 25, 2022

5 minread

Entrepreneurs are often touted as fearless, creative, innovative, passionate, and determined. These are the same qualities we look for when we hire our advisors.

At Cultivate, we believe entrepreneurs make the best advisors because they have the real-world experience to connect with our community and partner to work through challenging problems in the business. To continue supporting and positively impacting the small business community, we look for skilled experts with unique experiences from all different aspects of small business.

If you’ve ever wanted to know more about the backgrounds of our advisors, here are some of the talented members of our advising team.

Andy Montgomery | Business Advisor | Windsor, CO

The bulk of Andy’s career has been in the commercial banking industry and includes founding and serving as CEO of two community banks. Most recently, Andy was an early-stage founder in HDCS, which raised capital and consulted financial institutions that lend to higher-risk industries (like cannabis and cryptocurrencies). He is a creative and analytical thinker who loves to solve challenging problems; over this career, he has evaluated and advised hundreds of businesses across industries and is excited to bring this experience to Cultivate.

Being a commercial banker gives you a bird’s eye view of best practices and opportunities for improvement. I look forward to sharing my combined experience as an entrepreneur and someone who has spent their career learning about and analyzing hundreds of other people’s companies.

Andy Montgomery


Alex Dzierbicki | Business Advisor | Austin, TX

Originally from Michigan, Alex went to the University of Chicago to play football and, shortly after graduating, launched his career in the fitness industry. He began personal training and selling franchises for a nationally recognized fitness brand before investing in not 1 but 2 turn-around gyms in Michigan and Austin. Alex’s greatest passion in life is learning, and he’s excited to work closely with his clients to provide objective advice through personal connection while constantly learning new industries and business strategies.

Cristy O’Connor | Business Advisor | Denver, CO

Cristy has spent years in the wellness industry as a business consultant. Most recently, she’s worked with a private multi-location franchisee in helping them to buy struggling locations and implement processes/ procedures and hire the right leadership to increase their production & profitability. Cristy uses her curiosity to drive her brain’s analytical side to identify opportunities for process improvement to promote business growth. As someone who has worn all the business hats, she thrives in partnering with owners to help them create a holistic approach to scaling their business effectively.

Dan Smythe | Business Advisor | Phoenix, AZ

Dan comes from a successful career in logistics. During his tenure as the head of the Commercial Sales Division for a Fortune 1000 Company, he increased revenue from 36 million to 100 million. After leaving logistics, Dan spent a handful of years consulting under his own brand for other logistics companies across the nation. For the past three years, he owned and operated a local moving franchise out of Phoenix before selling it to a fellow franchisee within his network. Dan is excited to bring his passion for helping others to the Cultivate community, where he can help owners achieve their dreams and push them to go even bigger.

With my background and experience, I want to help entrepreneurs successfully navigate the business ownership waters and achieve all of their personal & professional aspirations.

Dan Smythe 


All of our advisors come from different industries with different experiences, but the one thing they have in common is that they’ve all run small businesses. If you or someone you know is a successful entrepreneur, looking to potentially transition to a new chapter where they can be entrepreneurial, but part of a team full of like-minded entrepreneurs, learn more about joining the team

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