Good Ideas + Bad Decisions

Kat Oldershaw and Ellen Hockley
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Welcome to Good Ideas + Bad Decisions! Let’s be real - it’s the perfect name for a show hosted by two business owners who have absolutely made both. Between us, we’ve started businesses, burned out, bounced back, and helped other entrepreneurs do the same. We’re here to talk about the messy middle of running a business - entrepreneurship, mental health, and the chaos that comes with making your own path. Join your hosts Ellen and Kat as we candidly share our experiences, answer your burning business questions, and welcome other owners into our emotional support business club.

  1. 4 days ago

    S2E7: Scaling Up with CleanCo Holdings' Dayna DeStefano

    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 Welcome 01:01 Meet Dayna 02:35 Entrepreneur Origin Story 03:11 Agency Success and Burnout 03:44 Web3 Experiment Unblocked 04:43 Co-Founder and New Baby Pivot 05:36 Boring Business Big Money 06:48 AI for Small Business Ops 08:20 Working With Your Spouse 10:52 Commercial Cleaning Niches 12:19 Recession Proof Lessons 13:05 Rinse and Repeat Expansion 14:47 Scaling Local vs National 17:35 Growth Options Ahead 18:14 Roll Up Strategy Focus 19:47 Boomer Seller Deals 23:54 Integrating Acquisitions 28:24 Tech Stack And AI Data 32:02 Selling Data To Robotics 35:33 What Drives Dayna 41:33 Parting Wisdom And Future 44:12 Where To Find Dayna 45:23 Episode Wrap Up

    46 min

  2. 26 Jun

    Coffee Chats with Ellen + Kat: Episode 024

    In this mini-episode of ‘Good Ideas + Bad Decisions,’ Kat and Ellen discuss how small-town dynamics can intensify business relationships and conflicts. Ellen shares a conflict in her business community and she and Kat conclude that Ellen should focus on showing up authentically rather than dwelling on the conflict. Kat also talks about launching her fabrication company Benchwork with two former coworkers and anticipating a difficult reaction from their previous boss, while the episode briefly touches on automation services and Ellen's email and domain forwarding issues.  Don't forget to⁠ submit your business questions⁠ for future episodes!  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.

    19 min

  3. 19 Jun

    S2E6: Using Human Design to Run a Business That Fits with Emily Bissen of Blue Heron Business Partners

    In this episode of 'Good Ideas + Bad Decisions,' hosts Kat and Ellen talk to Emily Bissen, founder of Blue Heron Business Partners, whose work sits at the intersection of business opportunity strategy and human design. Emily, a self-described 4/1 manifesting generator, explains how discovering her own human design gave language to skills she'd always had: reading people, spotting opportunities, and making the right connections at the right time. The conversation gets into the tension between prescribed entrepreneurial playbooks and trusting a more personalized approach, including the permission it takes to set boundaries, walk away from misaligned work, and build a business around what actually matters. Emily Bissen is a Business Opportunity Strategist and Super Connector who helps talented, driven business owners stop spinning their wheels and start moving. Using each client's unique Human Design, she creates strategies built for how they're wired rather than forcing someone else's playbook. Find Emily on LinkedIn or visit her at blueheronbusinesspartners.com. 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 Welcome01:22 Meet Emily Beeson02:00 Human Design Basics04:25 Retreat Spark Story05:39 Using Design With Clients08:37 Starting Her Business11:05 Ditching Others Playbooks14:25 Offers And Containers18:04 Time Freedom With Kids20:28 Teachers To Entrepreneurs22:53 Ditching the Playbook23:48 Permission to Choose26:20 Boundaries and Availability28:28 Permission to Quit29:01 Human Design Deep Dive30:29 Energy and Grounding34:50 Decision Making Styles40:35 Oldest Daughter Patterns42:56 Building a Support Village44:25 Get Curious Closing46:00 Where to Find Emily46:45 Podcast Sign Off

    47 min

  4. 12 Jun ·  Bonus

    Coffee Chats with Ellen + Kat: Episode 024

    In this mini-episode of 'Good Ideas + Bad Decisions,' Kat and Ellen discuss a book, "This Story Might Save Your Life," that mirrors their own podcast experience, then debate whether audiobooks count as reading (spoiler: Kat and Ellen agree that they do). They also explore how to make networking feel less awkward through clear purpose, low barriers, casual formats, and community containers where members can genuinely support one another. Don't forget to⁠⁠ submit your business questions⁠⁠ for future episodes!  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.

    25 min

  5. 5 Jun

    S2 E6: Embracing Change, Marketing Operations, and Building Remote Connections with Emily Oberman

    In this episode of 'Good Ideas + Bad Decisions,' hosts Kat and Ellen sit down with Emily Oberman, founder of The Content Atelier, a copywriter and content strategist who built a boutique agency around long-form content, newsletters (including Substack), and podcast support after recognizing a gap in the market for writers who actually understand the nuance of founder-led storytelling. The conversation spans remote work, packaging services as a generalist, navigating AI, a tough 2025 economy, and her advice to founders. Emily Oberman is a copywriter, content strategist, and founder of The Content Atelier, a boutique content marketing agency that focuses on long-form content. She has over 10 years of experience in content and systems strategy and has ghostwritten for over 150 individuals and brands. Her clients consider her their digital Mary Poppins. 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 Welcome 00:47 Chaotic Catch Up 01:27 Meet Emily Oberman 03:11 Long Form Content Focus 04:24 Substack Versus Blogs 07:06 Podcast Strategy Work 07:42 From Corporate To Remote 08:27 Commuting And Childcare 11:02 Remote Agency To Solo 11:55 Imaginary Friends Origin 13:35 Digital Mary Poppins Brand 16:46 AI And Marketing Ops 19:40 Clients Using AI Drafts 22:27 Why And Who First 24:48 Values Driven Services 25:43 Pricing For Small Business 27:00 Choosing Tools By Values 28:59 Claude Versus ChatGPT 30:18 Generalist Boundaries 31:53 Intuition And Human Design 33:41 Remote Work Setup 37:19 Contractors And Volatility 41:34 Female Founder Stigma 43:50 Advice And Wrap Up

    47 min

  6. 29 May ·  Bonus

    Coffee Chats with Ellen + Kat: Episode 023

    In this mini-episode of ‘Good Ideas + Bad Decisions,’ Kat and Ellen discuss Kat’s first hypnosis session with Kelly Chessen of Hope Rd. Hypnosis that focused on her relationship with money. Kat describes a guided visualization exercise involving inviting past influences on money to a mental table, confronting negative associations, inner-child emotions, and asking money what it needs. Kat feels empowered by her takeaway about using money for creativity, joy, and connection and notes new opportunities arising. They close by discussing how to talk with clients about money, pricing, and boundaries. Don't forget to⁠ submit your business questions⁠ for future episodes!  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.

    20 min

  7. 22 May

    S2 E5: Finding Your Creative Flow with Wildly Creative Wellness Founder Vicky Winkler

    In this episode of 'Good Ideas + Bad Decisions,' hosts Kat and Ellen welcome Vicky Winkler, founder of Wildly Creative Wellness, an art journaling and creative wellness community. Vicky shares how art journaling helped her move from feeling "only okay" to finding real purpose and fulfillment. She describes art journaling as focused on process over outcome with no perfectionism required, and explains how that mindset can build confidence to experiment in other areas of life too. She outlines her Wildly Creative’s monthly themes, weekly prompts, live creation calls, and co-working sessions, and the group discusses why rigid routines like The Artist's Way can fall short and how to start simply instead. Vicky Winkler is the founder of Wildly Creative Wellness, a space where everyday people discover that creativity has always lived inside them. Through art journaling workshops, online retreats, and one on one support, she helps people slow down, reconnect with themselves, and find fulfillment through self-expression. Her work is rooted in the belief that making art isn’t just for “artists.” It’s for anyone who wants to feel more alive. 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 Welcome 01:09 Meet Vicky Winkler 02:34 Why Art Journaling 04:59 Perfectionism Blocks 06:26 Journal Not Canvas 08:00 Creative Without Selling 10:36 Membership Breakdown 14:07 Calls And Sanctuary 15:20 Artists Way Debate 20:06 Five Minute Practice 21:17 Tools For Regulation 23:51 No Rules Mindset 25:30 Leap of Faith Art 25:49 Cortisol and Creativity 26:42 Blank Page Tricks 27:27 Five Minute Time Paradox 28:45 Timers Flow and Breaks 32:03 Finding Art Journaling 35:01 Creative Identity Blocks 36:35 Easy Supplies to Start 38:56 Healing Through Drawing 42:18 Try It and Connect 43:38 Episode Wrap Up

    45 min

  8. 15 May ·  Bonus

    Coffee Chats with Ellen + Kat: Episode 022

    In this mini-episode of “Good Ideas + Bad Decisions,” Kat and Ellen dive into the topic of discovery calls and networking. Kat walks through her approach of offering a single free 30-minute call for prospective clients, collaborators, and general connections alike. Kat and Ellen address client fit, barters and trades, and keeping up a connection. The episode also explores the value of maintaining boundaries, being intentional about how time is given, and keeping follow-up communication clear and straightforward. Don't forget to⁠ submit your business questions⁠ for future episodes!  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.

    18 min
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About

Welcome to Good Ideas + Bad Decisions! Let’s be real - it’s the perfect name for a show hosted by two business owners who have absolutely made both. Between us, we’ve started businesses, burned out, bounced back, and helped other entrepreneurs do the same. We’re here to talk about the messy middle of running a business - entrepreneurship, mental health, and the chaos that comes with making your own path. Join your hosts Ellen and Kat as we candidly share our experiences, answer your burning business questions, and welcome other owners into our emotional support business club.

Information

  • Creator
    Kat Oldershaw and Ellen Hockley
  • Years Active
    2025 - 2026
  • Episodes
    57
  • Rating
    Explicit
  • Copyright
    © Kat Oldershaw and Ellen Hockley
  • Show Website
    Good Ideas + Bad Decisions