Show notes
In this episode of 'Good Ideas + Bad Decisions,' Kat and Ellen talk to Dayna DeStefano, an entrepreneur who has launched and sunset multiple ventures since leaving corporate product leadership in 2019. Dayna shares how that winding path led her to co-own her husband's family commercial cleaning business and now spearhead an acquisition strategy through CleanCo Holdings, buying up complementary building service businesses and integrating them with centralized operations and data. She also offers her advice to founders: design your career around your own blueprint, stay simple and focused, and act on what you feel called to do. Dayna DeStefano has spent nearly 20 years building brands and businesses, from serving as VP of Product at a digital media company acquired by Gary Vaynerchuk to founding multiple ventures, including a branding agency, a consulting company, and a tech literacy media company for women. Today, she splits her time between advising select founders and small business owners on go-to-market strategy and AI implementation, co-owning a portfolio of commercial building services businesses with her husband, and building The Business of Energy, where she writes about using energy as a navigation system for life and work. Kat is the Founder of kat&co, a Creative Operations Consultant, and the Co-Owner and Director of Operations at Benchwork Fabrication. She helps interior designers and creatives turn ideas into streamlined, sustainable businesses. With a background in psychology and deep experience in creative business operations, she’s known for navigating the intersection of creativity and systems with both strategy and empathy. Join her newsletter, The kat&co Download.Ellen Hockley is a three-time entrepreneur, small business consultant, community builder, and the founder of Ellen Hockley Consulting and SAGE Women. She guides female founders to build intuitive, values-driven businesses aligned with the life they want for themselves and their families. Join her Substack newsletter, The Quiet Wins.00:00 Podcast Welcome01:01 Meet Dayna02:35 Entrepreneur Origin Story03:11 Agency Success and Burnout03:44 Web3 Experiment Unblocked04:43 Co-Founder and New Baby Pivot05:36 Boring Business Big Money06:48 AI for Small Business Ops08:20 Working With Your Spouse10:52 Commercial Cleaning Niches12:19 Recession Proof Lessons13:05 Rinse and Repeat Expansion14:47 Scaling Local vs National17:35 Growth Options Ahead18:14 Roll Up Strategy Focus19:47 Boomer Seller Deals23:54 Integrating Acquisitions28:24 Tech Stack And AI Data32:02 Selling Data To Robotics35:33 What Drives Dayna41:33 Parting Wisdom And Future44:12 Where To Find Dayna45:23 Episode Wrap Up