What do you do when your only options are a job you don’t want or a business that doesn’t exist yet? Angus Willows, the founder of Kangaroo Hanger, chose the harder path — and made it work. As a college student with a 3D printer under his bed, he designed a better hanger, taught himself how to file a patent, launched a second business to fund it and bet everything on a TikTok challenge that changed his life.

But this isn’t just a story about going viral. It’s about building something real without a safety net and how you could trust yourself long before the world gives you permission. Host Andrea Marquez unpacks how Angus bootstrapped his way from a scrappy cardboard prototype to retail shelves and why he kept going, starting business after business, even when the stakes got higher. If you’ve ever wondered whether you’re ready, Angus’ story might show you that readiness isn’t the goal — resilience is.

Got a bold leap of your own? Share it with us in an Apple Podcasts review, Spotify comment, or email us at thisissmallbusiness@amazon.com – you might hear it in a future episode.

In this episode, you’ll hear:

(02:30) Can entrepreneurship start at six years old? Angus shares how selling bow ties as a kid sparked a lifelong obsession with inventing.

(04:46) Would you major in something you’re bad at — just for the challenge? Angus explains why struggling through engineering made him a better builder.

(06:26) What problem do you want to solve? Angus shares the frustrating dorm room moment that sparked the idea for Kangaroo Hanger.

(08:40) Could adding less make your product sell more? Angus talks about the power of simplicity.

(11:25) What if your side hustle exists just to fund your dream? Learn how Angus started a second business to avoid getting a full-time job after graduation and fund Kangaroo Hanger.

(14:46) Is it possible to write your own patent? Hear how Angus did it — with a book and no legal training.

(16:32) What happens when you give yourself 30 days to go viral? Angus’s TikTok experiment and how going viral helped him reach his pre-order goal.

(22:34) When does going retail make more sense than selling direct? Angus explains how shipping costs drove a big strategic shift and how to get into retail.

(24:57) How many businesses can one person build? Angus talks about his third company — and what he’s learned from jumping into new ventures and taking risks.

(27:07) How do you manage the stress of debt as a founder? Angus shares his mindset around pressure, calculated risk, and staying grounded.

(28:15) Not sure you can bet on yourself to take a big risk? Angus explains how self-trust is built — and why it starts with the smallest decisions.

What if the riskiest part of your business was just saying what it is out loud? Katie Diasti didn’t plan to start a company about periods – especially not one she’d pitch to rooms full of confused, uncomfortable investors. But when a college class project opened her eyes to just how outdated and wasteful the period care aisle was, she couldn’t unsee it. That spark turned into Viv, a sustainable, stigma-smashing brand that’s changing how people learn about and experience their periods. Host Andrea Marquez unpacks what it really takes to build something bold in a space full of silence. You’ll walk away with a deeper understanding of how education can be a growth strategy, how community can be a business tool and why sometimes the boldest thing you can do is say the quiet part out loud and start a conversation. If you’ve ever felt like your idea was too taboo, too weird, or too risky – Katie’s story will show you that that might not be the red flag you think it is. It might be proof that you’re onto something big.

Got a bold leap of your own? Share it with us in an Apple Podcasts review, Spotify comment, or email us at thisissmallbusiness@amazon.com – you might hear it in a future episode.

In this episode you’ll hear:

(01:55) What if the riskiest part of your business was just saying what it is out loud? Hear how Katie’s personal experience around avoiding period talk shaped Viv’s mission to rewrite the narrative around period care.

(05:00) Can a class project turn into a startup? Katie explains how she validated her idea with real feedback — and got obsessed with solving a problem.

(07:30) Struggling to figure out how to create and test your products? Katie shares how she hustled for product feedback, sourced sustainable materials, and tested prototypes on herself and her friends.

(09:20) Scared to ditch a stable job? Katie was too. She reveals the exact moment she backed out of her job offer – and why she did it.

(13:31) Ever pitched a room full of uncomfortable investors? Katie breaks the ice with “Let’s talk about periods” — and wins them over anyway.

(18:10) Can education be your best growth strategy? Katie shares how content helped her build trust, strengthen customer relationships, and expand her product line.

(26:30) Feeling unsure about your idea? Katie’s advice for building in a risky and stigmatized space might be the push you need to finally go for it.

What if the real barrier to your success isn’t risk but uncertainty? Dr. Matt Rutherford, John de Pope Chair in Entrepreneurship at Oklahoma State University, joins host Andrea Marquez to redefine risk for founders and show you how to make every risk you take more manageable. You’ll get to hear the six types of entrepreneurial risk, learn why distinguishing risk from uncertainty is crucial, and discover how pinpointing the risks you face can actually tilt the odds in your favor. By the end of this episode, you’ll have a simple framework to spot, measure, and hedge risk so that your next big leap feels less like a gamble and more like a calculated step forward.

Got a bold leap of your own? Share it with us in an Apple Podcasts review, Spotify comment, or email us at thisissmallbusiness@amazon.com – you might hear it in a future episode.

In this episode, you’ll hear:

(01:29) Ever felt entrepreneurship wasn’t for you? Andrea and Matt share how family and early doubts made them think twice about starting a business – for now.

(06:18) What’s the real difference between risk and uncertainty? Learn why risk can be quantified and how that clarity fuels confident decisions.

(08:53) Which six risks should every founder know? Discover which risks apply to your business and how to spot them before they blindside you.

(12:16) How do you turn uncertainty into risk by diversifying? Practical tips on expanding products, channels, or personal investments.

(15:26) How can small tests tilt the odds? Discover the low-cost experiments that validate ideas without blowing your budget.

(16:30) How do you embrace the upside of risk? Discover why focusing on opportunity instead of fear can turn setbacks into springboards for growth.

(20:03) Can you start a business even if you’re risk-adverse? Matt shares how teaming up with his wife turned caution into confidence and helped them start a small business together.

(22:46) How do you overcome the fear of risk and just start? Matt lays out three ways you can take a calculated leap forward: suck out every risk, enlist trusted voices, and run small experiments.