#82 Oren Klaff - how to Flip the Script and close the deal
Release Date: 08/21/2019
Irrational Confidence, Extreme Ownership and Building Real Leverage
The Sweaty Startup
In this episode with Chris and Chris, I talk about overcoming doubt, building irrational confidence, and using fear setting to make hard decisions less scary. We unpack lessons from chaotic early business seasons, anxiety filled moments, and the mindset shift toward extreme ownership that changed everything for me. We also cover leverage through hiring, auditing your time, focusing on sales and marketing, raising resilient kids, and why success means watering every garden in your life not just business. Grow your business: Book: ...
info_outline
Why Struggle Is the Point
The Sweaty Startup
Jamie and I talked about why struggle is not something to avoid but something to embrace. We got into parenting, confidence, health, balance, and why giving yourself permission matters more than waiting for approval. We discussed what a good life actually looks like, how pressure shapes better people, and why playing the long game across generations is more meaningful than chasing status or shortcuts. This episode is about values, responsibility, and becoming someone your kids can be proud of. Grow your business: Book: Newsletter: ...
info_outline
Why Most Entrepreneurs Burn Out and How to Actually Build a Life You Want
The Sweaty Startup
Nick Aufenkamp and I dug into the real reasons most entrepreneurs end up overwhelmed, broke, or miserable. We talked about delegation, generational wealth, and why the “boring” businesses often lead to the most freedom. I shared how I built leverage through international hiring, what I look for when choosing a game worth playing, and why long-term stress and sacrifice only make sense if you're chasing the right outcome. This is one of the most honest conversations I’ve had about work, family, and building a business that actually improves your life. Grow your business: ...
info_outline
How I Built Businesses By Choosing Better Odds And Doing Hard Things
The Sweaty Startup
Trevor and I talked through how I build real businesses by choosing better odds instead of chasing hype. I shared how I started from zero, tested demand with simple tactics, and why boring proven ideas beat trying to be the one in a thousand startup. We also covered pricing, firing bad customers, using data over ego, and why business never gets easier, you just get stronger. From building companies to raising kids who can handle discomfort, this episode is about doing hard things and winning because of it. Grow your business: Book: ...
info_outline
How I Built a Life Around Freedom and Used Boring Businesses to Fund It
The Sweaty Startup
Mikk and I sat down to talk about what it really means to build a business that supports the life you want instead of trapping you in a cycle of stress and burnout. I walked him through the lessons I’ve learned from operating service companies, investing in real estate, and hiring globally to lower overhead. We got into how I’ve used boring, simple businesses to build leverage, why momentum is the most dangerous drug in entrepreneurship, and how I protect my time so I can focus on what matters. We also talked about content, writing the book, and the pressure that comes with growing a...
info_outline
How I Built Wealth by Doing the Boring Work That Actually Pays
The Sweaty Startup
Matt and I talked about the kind of businesses that actually build wealth and why most people overlook them chasing trends that never pay off. I shared my story from Storage Squad to Somewhere and broke down how trading time for money is still the best place to start. We talked about the real odds of success, what Silicon Valley gets wrong, how to think about leverage, and when to finally hire so you can get back to doing high-value work. This one’s about clarity, execution, and doing what actually works in the real world Grow your business: Book: ...
info_outline
How I Built Wealth Doing Boring Work Most People Ignore
The Sweaty Startup
Cody and I dug into the real side of entrepreneurship, what it actually takes to build wealth without chasing shiny ideas. I shared why I walked away from the tech startup fantasy and leaned into simple businesses that solve real problems. We talked through the ten minute drill, how I evaluate opportunity in any town, and why people waste years building businesses with zero demand. I broke down why your first business is about reps and skill acquisition, not money, and how boring work like tree removal or survey work can set you up for financial freedom faster than chasing passive income. This...
info_outline
How James Laidlaw Built InHomeGolf into a Multi Million Dollar Business
The Sweaty Startup
This is the full conversation I had with James Laidlaw about how he walked away from a high-paying commission job and built InHome Golf from scratch. We broke down how he scaled a golf simulator business during COVID, reinvested everything back into growth, and navigated the chaos that comes with explosive customer demand. Here’s a photo of my simulator setup that James’s company installed for me. & Here’s 22 other things that have that materially improved my quality of life: If you want to reach out to James, email him at If you’ve ever thought about leaving your job or...
info_outline
How to Get Unstuck and Build a Career You Actually Want
The Sweaty Startup
Brian and I got into what it really takes to make progress when you're stuck in a job, a business, or a mindset that’s not working. We talked about how people overanalyze and under-execute, why momentum matters more than motivation, and the mindset shifts that helped me stop chasing the perfect idea and start stacking wins. I shared the story of how I built my early businesses, how I tested ideas without overcommitting, and how you can take control of your career path by doing common things uncommonly well. This one is for anyone who feels like they’re waiting for permission to start. ...
info_outline
Why I Stopped Chasing Billion Dollar Ideas and Started Optimizing for Real Freedom
The Sweaty Startup
Corey and I got into what actually matters when you're building a business and a life. We talked about what true wealth looks like beyond the money, why health and time freedom matter more than status, and how I’m thinking about the next 10 years. I broke down how I approach business growth, the truth about AI and electricity, and what most entrepreneurs get wrong about lifestyle creep. We also got into some honest talk about luck, operating skill, and why doing simple things well beats chasing the next big thing. Grow your business: Book: ...
info_outlineSales is tough - why not turn it around and let the customer sell you? Bestselling author Oren Klaff tells us how to approach customers and let them convince themselves to buy from you.