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Recent Episodes

How to Upgrade Your Small Business with Smarter Tech for Happier Customers
Nov. 20, 2025

How to Upgrade Your Small Business with Smarter Tech for Happier Customers

Bossy is in Dallas and chatting how to scale your small business!
Betting on What Works for You with the Former CEO of Coach, Lew Frankfort
Nov. 13, 2025

Betting on What Works for You with the Former CEO of Coach, Lew Frankfort

In this episode, Tara chats with former Coach CEO Lew Frankfort about redefining what luxury means — and who gets to access it. Lew shares how he took a small, slow-growing family business and transformed it into a global brand by pioneering the concept of accessible luxury. He didn’t just ride a rocketship — he built one. Tune in to hear how trusting his gut, leaving a safe job, and spotting an unmet need in the market helped him reshape an entire industry.Discover more about how AT&T Busines
How to Turn a Chip on Your Shoulder into $310M with Bonobos founder, Andy Dunn
Nov. 6, 2025

How to Turn a Chip on Your Shoulder into $310M with Bonobos founder, Andy Dunn

In this episode, Tara chats with Bonobos co-founder and serial entrepreneur Andy Dunn on what it really takes to build a $310M brand. Listen in as Andy opens up about the mental toll of entrepreneurship, why delusion might be your greatest asset, and how founders can turn a chip on their shoulder into serious ROI. Plus, his honest take on why being your own boss really is better than climbing someone else’s ladder. Discover more about how AT&T Business can help your small business: http://att.co
Climbing the Ladder like a Boss with AutoDesk CMO, Dara Treseder
Oct. 30, 2025

Climbing the Ladder like a Boss with AutoDesk CMO, Dara Treseder

In this episode, Tara chats with Autodesk CMO Dara Treseder about her meteoric rise through the marketing world. Tune in to hear Dara’s take on betting on yourself, navigating hard career choices, and how to position yourself to win — even when the odds are stacked. She also shares why bold leadership isn’t just about power, but purpose — and how to know when it’s time to stay or go.Discover more about how AT&T Business can help your small business: http://att.com/why-att-business💌 Want to
Making Bank & Hosting Bangers: Profitable Event Planning with Marina Middleton
Sept. 25, 2025

Making Bank & Hosting Bangers: Profitable Event Planning with Marina Middleton

Marina Middleton shares when it makes sense to re-invest in your own company
How to Be Innovative & Then Standardize the Process
Sept. 18, 2025

How to Be Innovative & Then Standardize the Process

In this episode Tara sits down with Sweetgreen co-founder Nicolas Jammet to talk about the process of transitioning from the creative, idea-generating early founder role, to becoming the leader of a larger, publicly traded company. 00:00 Intro 01:04 What innovations at Sweetgreen Nic is most proud of 06:18 Where Nic looks to find inspiration for innovating his business 10:44 How innovation happens at Sweetgreen now that they’re a billion-dollar business 13:09 Office Hours segment 16:30 The entre