John Meese starting a coworking space on the cusp of 2020 – and his year only got more challenging from there. Tune in to hear his story of becoming a first generation college grad, rebuilding after 2020, and advice that will change the way you perceive 'waiting'.01:10 – Meet John: Author and Educator06:43 – John's Humble Beginnings10:09 – Entrepreneurial Journey14:11 – How Family Challenges Impact Career Decisions20:47 – Opening a Coworking Space In 202024:20 – Rebuilding and Growth30:33 – F...

Today Terry is joined by Jeff Scult, founder of clothing company One Golden Thread. Together they explore personal transformation, why focusing on solutions is key for moving forward, sustainable fashion, and how to reclaim a life of purpose and authenticity.1:00 – Meet Jeff Scult: Founder of One Golden Thread4:00 – The Birth of One Golden Thread6:33 – The Journey of Professional Discovery9:40 – Creating the Perfect T-Shirt12:55 – Unlocking Creativity and Freedom20:48 – Sustainable Fashion an...

Jourdan Hathaway serves as Chief Marketin Officer at General Assembly – but nothing has been handed to her along the way. In today’s interview, Jourdan shares her journey from extreme poverty to becoming CMO, and discusses the power of vulnerability and frameworks to create change. 01:39 – Meet Jordan Hathaway: CMO of General Assembly03:39 – Professional Journey: From Ad Agency to CMO09:46 – The Power of Frameworks for Leveling Up13:54 – Starting In Extreme Poverty18:12 – Catalysts for C...

Today Terry is joined by Sanyika Street, founder and CEO of The All-In Man, to discuss his incredible journey from being financially and emotionally broke to becoming a sought-after coach for high-achieving men. 01:33 – Meet Sanyika04:13 – Breaking the Masculinity Box05:58 – The Rock Bottom Sandwich09:52 – Journey to Integrity 19:57 – The Power of Feedback and Healing22:12 – The Importance of Mentorship26:35 – Practicing Patience and Strategic Thinking31:36 – Final Thoughts and Pers...

Nathan Barry is the founder and CEO of Kit (formerly ConvertKit). The platform now serves 600,000+ creators, including Tim Ferriss, Pat Flynn, and Terry himself. But that kind of growth doesn’t come without a cost. Today we will dive into the steep physical and mental cost that Nathan faced from tying his identity to productivity – and how he handled the fallout when he could no longer be productive. 1:18 – Meet Nathan Berry: Founder and CEO of Kit3:25 – The journey of buildin...

Without your work, who are you? Mike “C-Roc” Ciorrocco says that most people place their identity in what they do – when instead your identity should be who you are at your core, guided by your mission and core values. In today’s interview, Mike shares his journey to living in line with his identity. 1:35 – Meet C-Roc4:08 – Core values7:28 – Why most haven’t documented their core values15:45 – Role of faith17:09 – C-Roc’s challenge21:23 – Converting life events to rocket fuel23:26 – Lett...

Jo Franco is a speaker, writer, Netflix host, and polyglot. Today, she’s sharing the story of growing up in the US as an undocumented immigrant, creating a booming travel channel on YouTube, and how getting shot in the back created the inflection point she needed to start stepping into a new phase of life. 1:30 – Meet Jo4:35 – Miserable success15:22 – No fast forward button18:24 – Getting shot25:40 – The power of journaling for processing emotions31:12 – The year life imploded37:17 – Sec...

Mo Bunnell is an author, podcast host, and founder of the Bunnell Idea Group, which has trained 25,000 people at over 500 companies for scaling the right way. Today, he shares the story of what he calls, “the dumbest thing I ever did that almost destroyed my family” – and the story of recovery. 1:46 – Meet Mo4:42 – How Mo started his business8:44 – Mo’s challenge19:21 – Why we don’t take the clear next right step23:07 – The power of improving one thing24:36 – Give to grow28:27 – Looking ...

Jake Thompson describes his early life as an entrepreneur as “superficial and crappy”, busy building sandcastles of external success markers. After facing enormous debts and the worry that comes along with them, he learned to live the motto of his business, Compete Every Day. Today, Jake shares his story of leveraging his business to the brink – and the slow climb back up to the top. 1:41 – Meet Jake3:48 – Journey to entrepreneurship14:40 – Clawing out of a debt hole25:43 – Combatting hy...

As the founder of restaurant chain Slutty Vegan, Pinky Cole Hayes wears a lot of hats – and she wears them well. Today, she joins us to talk about growing from failure, making an impact on your surroundings, and how to identify what is meant for you in life. 1:40 – Meet Pinky2:20 – The importance of discernment7:08 – What to expect at Slutty Vegan8:34 – Growing from failure12:20 – Struggles with getting sued and navigating public life15:00 – New work with REVOLT18:26 – Group economics&nb...

You may know Barrett Brooks from his time as COO for ConvertKit during its formative years, his work as an executive coach, or his podcast Good Work. In today’s interview, we’re grateful for the opportunity to go beyond high level accomplishments and hear Barrett’s story of recovery from childhood trauma, and his thoughts on moving forward. 2:30 – Meet Barrett11:45 – The one question that helps unlock the possible13:09 – The road to a breakthrough, and fallout18:46 – Barrett’s chal...

Today we’re diving into the incredible journey of Andrea Olson, a successful entrepreneur, mom of six kids, author of five books, and founder of a seven-figure company. Andrea shares her story of overcoming adversity, from dealing with toxic relationships to discovering the power of passive income, which allowed her to support her children independently. Join us as we explore the challenges of balancing parenting and business ownership, and gain valuable insights on mindset, resilience, ...

For years Jess Ekstrom avoided speaking about a formative event in her family life – her family being swindled out of money by her uncle, Bernie Madoff. Today, Jess joins us to talk about the decision to start speaking about formative challenges, and how true optimism isn’t naive.2:40 – Introductions4:24 – The roots behind looking for the bright side8:20 – Navigating the shift to talking about hard things13:46 – Fallout from Bernie Madoff scamming their family22:37 – Teaching from struggle, n...

Craig Siegel was a Wall Street big shot who woke up in his thirties and realized he was lost. During the pandemic, he finally got the quiet he needed to kick-start his transformation. Today, Craig joins us to talk about guilt, swapping drinking for running, and how to reinvent yourself. 1:35 – Introductions4:27 – Current context7:20 – Craig’s challenge12:30 – Drinking issues and turning point18:00 – The Reinvention Formula22:02 – Guilt25:12 – Parting shot***** Learn more from our g...

Jay Siano is a real estate and branding expert who has worked with brands like Starbucks, Chipotle, and Orangetheory Fitness. During his college years, Jay’s mom got sick with cancer, and he had to face the choice between staying in school or coming home to work in the family business. Jay bet on himself, and stayed in school. Already prone to numbing out, Jay continued down a self-destructive path until he got pulled over for a DUI and spent a couple of nights in jail. Today, Jay joins ...

Despite spending years investing in the rat race, Nat Berman knew he had to strike out on his own. In today’s episode he shares the story of that time, and climbing toward a business that has made him millions. 1:35 – Introductions4:55 – Current context6:27 – Nat’s biggest challenge12:13 – How 9/11 impacted Nat’s thinking15:01 – Quitting18:35 – The ISE model22:49 – Coaching philosophy25:20 – Why losses are important29:17 – One lesson Nat wishes he’d learned soonerLearn more from our gues...

Tripp Lanier describes his interior life after a breakup in his twenties as a house of cards tumbling to the ground. Suddenly, he was forced to confront emotional issues he had been actively avoiding for years – including his own mother’s suicide. In today’s interview, Tripp walks us through that time in his life, and how to chart a path forward that feels alive with possibility. 1:34 – Introductions4:30 – Tripp’s challenge10:10 – What to do with the phrase “everything happens for a...

As a human performance coach, Robert Palmer is literally a pro at helping others achieve high performance. But you don’t get there without some major bumps in the road. In today’s episode, Robert shares: His experience filling in as a father figure for his brotherThe impact of suddenly losing an older sister Re-examining his own beliefsCommitting to living a healthy life and following through2:55 – Introduction6:00 – Source of curiosity9:52 – Growing up with a dad in the NFL12:24 – ...

What have you given up for the successes you’ve achieved? Today Kim Kaupe joins us to share her experience with priorities, regrets, and spending your life well. 1:43 – Introductions3:53 – Kim’s current situation7:09 – Kim’s challenge15:20 – Authenticity on social media17:40 – Source of boldness22:53 – Homework*****Learn more from our guest: Follow Kim on Instagram: https://www.instagram.com/kimkaupe/?hl=en Check out her podcast, Coffee With Kim: https://kimkaupe.com/coffee-wit...

As a leader, a serial entrepreneur, and the former head of growth at ConvertKit, Darrell Vesterfelt had a track record of success. But a moment of crisis led to his partners at one of the businesses he co-founded asking him to step away. Today, Darrell is publicly sharing that story for the first time, as well as the story of how he found his way back from a year in the fog of shame. 1:33 – Introductions2:53 – Current context4:22 – Darrell’s hardest challenge9:37 – First kids + starting ...

Growing up Hannah Nieves leaned on academics and achievement as a way to cope with a volatile home life. When burnout put her in the hospital, she had to reassess her work – and her habit of internalizing stress. Today, she shares the story of overcoming her burnout and learning to live life in a more whole way. 2:08 – Introductions/Hannah’s current situation5:12 – Childhood 7:33 – Hannah’s challenge12:34 – Helping other people with burnout14:03 – Preventing burnout as a mother...

Jason Feifer (author, editor-in-chief of Entrepreneur Magazine) joins us to share a challenge that lasted five years and changed the course of his life. The core theory: Life is reactive, not linear. 1:55 – Meet Jason6:15 – Jason’s most challenging time8:44 – Life is not linear14:55 – How Jason got his resilient mindset21:28 – Using what you have24:56 – A lesson from Ryan Reynolds27:45 – Looking for the solution that presents the least problems36:40 – Managing the whiplash of normal life...

Although Lauren Maillian is the picture of success today, about 15 years ago she was dealing with a life implosion when her husband walked out of her life, leaving her to be sole caretaker and provider for their two children.Today, Lauren shares how that implosion was the turning point in her life, and how she worked her way into success. 1:40 – Introductions3:55 – Lauren’s current situation5:44 – Lauren’s big challenge13:44 – Bitterness22:40 – Feelings around sharing a truth 29:18...

Tim Stoddart, CEO of Copyblogger, shares his story of growing up in Philly, getting sober, and how writing in secret exploded into a career. 2:08 – Introduction3:38 – Tim’s most challenging moment7:21 – The wake-up call12:50 – Intervention15:47 – After leaving treatment22:36 – Changing your environment25:50 – Addiction doesn’t hurt just you29:18 – When do you stop feeling like a screw-up?34:57 – Starting his business40:55 – Parting wisdom*****Learn more about our guest: Connect on L...