Startups With Stu
Hosted by Startups With Stu
A high-energy entrepreneur interviews fellow founders, focusing on their origin stories, early struggles, and the mindset required for startup success.
This is a founder-on-founder interview show where host Stu Draper uses his own entrepreneurial background to connect with guests. Each episode is framed as an inspirational case study, tracing a founder's journey from their earliest hustles to their current success. The show emphasizes the grit of the early days, often highlighting how guests overcame financial hardship or personal challenges to build their companies.
“The host's infectious enthusiasm and high-energy introductions set a relentlessly positive tone. Unlike more technical business podcasts, the focus is squarely on the founder's personal narrative and the mindset that fueled their success, often going back to childhood experiences.”
Who hosts this show
Stu Draper is a serial entrepreneur who hosts the podcast to share insights from founders and investors. Before age 40, he was a nine-time Inc. 5000 honoree for companies he founded. Draper founded the digital marketing agency GetFoundFirst.com, which he later sold, and then started Stukent, an 8-figure educational technology company that provides digital marketing simulations and courseware to universities. He is also the co-author of the bestselling textbook "Digital Marketing Essentials" and an angel investor in eight businesses.
Credentials & credits
- Founder & CEO of Stukent
- 9-time Inc. 5000 honoree
- Co-author of 'Digital Marketing Essentials'
- Founder of GetFoundFirst.com (acquired)
- Angel investor
- Former Adjunct Professor at Brigham Young University - Idaho
Other ventures
- Stukent
- GetFoundFirst.com
- CharityFast.org
What kind of podcast
When new episodes drop
- 01From Cop to $17.6M Entrepreneur | Sam DeMaio Startup Journey | Episode 69May 27, 2026 · 34 min
- 02How a Twenty-Something Entrepreneur Landed 35% Equity | Episode 68May 25, 2026 · 54 min
- 03Mom of 5 Builds Million-Dollar Apparel Brands | Episode 67May 20, 2026 · 42 min
- 04Building a National Outdoor Brand from Scratch | Episode 66May 18, 2026 · 54 min
- 0525 Years in Fitness, 2 Big Exits, Zero Investors | Episode 65May 13, 2026 · 48 min
- 06Why High Performers Still Feel Empty | Episode 64May 11, 2026 · 46 min
- 07Building More Than a Startup: Becoming Who You’re Meant to Be | Episode 63May 4, 2026 · 50 min
- 08He Built a Self-Cleaning Toilet Seat… And Raised $1M | Episode 62Apr 15, 2026 · 47 min
Notable episodes
- 01Mom of 5 Builds Million-Dollar Apparel Brands | Episode 67
Features Chynna Hansen, who built a 7-figure business and closes her company at 2 PM daily so her 30 employees can pick up their kids from school.
- 02From Cop to $17.6M Entrepreneur | Sam DeMaio Startup Journey | Episode 69
The story of Sam DeMaio, who built a $17.6M remodeling empire while working full-time as a police officer and serving in the National Guard.
- 03How a Twenty-Something Entrepreneur Landed 35% Equity | Episode 68
Details how college student Annamarie Davis worked for free at a recording studio and successfully negotiated for a 35% equity stake instead of a salary.
- 04Why High Performers Still Feel Empty | Episode 64
A unique format where the host, Stu, undergoes a live coaching session, revealing his own vulnerabilities and subconscious beliefs about success.
What you'll be asked on this show
Stu Draper runs a very encouraging and motivational interview. He starts with a powerful, pre-scripted introduction summarizing the guest's success to frame them as an expert. His first move is often to rewind to the very beginning, asking about the guest's childhood or what they were like before they were an entrepreneur. He probes for detail by expressing enthusiastic disbelief ("You did all this while you were still a police officer?") or asking for specific examples ("Give me an example of the 'little things'..."). Draper consistently connects a guest's life experiences to their business mindset, asking how a particular challenge or event shaped their entrepreneurial journey. He builds strong rapport by laughing often and relating their stories back to his own founder experiences.
Stu Draper opens each episode with a high-energy, detailed summary of the guest's major accomplishments before the interview even begins. The format is a friendly, chronological conversation that often starts with the guest's childhood to trace the origins of their entrepreneurial spirit. Draper frequently shares his own experiences as a founder to build rapport and create a relaxed atmosphere.
Questions Startups With Stu keeps coming back to
10 cataloguedIf you're going on this show as a guest, expect some version of each of these. Each note explains when Startups With Stu reaches for it.
origin
2- Q.01
“What was your childhood like, and were your parents entrepreneurs?”
This is often one of the first questions, used to establish the guest's origin story and find the roots of their work ethic.
- Q.02
“Tell us about your business.”
A broad opening question that allows the guest to frame their company in their own words.
mindset
2- Q.01
“How did that [life experience] help you with your entrepreneurship?”
He asks this to explicitly connect a guest's personal background or non-business challenges to their professional mindset.
- Q.02
“How did you decide you could give this a try, even though it was scary?”
Probes the emotional turning point and the personal courage required to commit to a new venture.
process
2- Q.01
“What was easy and what was hard when you first started out?”
This question digs into the practical challenges and unexpected advantages of the early startup phase.
- Q.02
“So this was a pivot when the growth of your first business slowed?”
He uses this type of clarifying question to confirm the timeline and strategic reasons behind a business pivot.
money
2- Q.01
“Where were you going to get the money to start?”
Focuses on the practical, and often scrappy, details of initial funding and bootstrapping.
- Q.02
“Have you ever sold a business?”
Used to inquire about a founder's experience with exits and their broader entrepreneurial history.
advice
1- Q.01
“How did you do that? Can you give the audience some tips?”
Prompts the guest to distill their experience into actionable advice for listeners.
future
1- Q.01
“Are you thinking the sky's the limit, or are you looking at other things?”
This question explores the guest's future ambitions, long-term vision, and potential for diversification.
Signature segments
- · Catchphrase: "...take your startup to the moon."
- · High-energy intro summarizing guest's accomplishments
- · Chronological interviews starting from childhood
- · Host sharing his own founder experiences
Topics covered repeatedly
Who gets booked here
The show features founders who have built seven-figure or larger businesses, often from a bootstrapped start. Guests typically have a compelling "started from nothing" story, such as turning a small side hustle into a large company or pivoting after a significant challenge.
- Sam DeMaioon From Cop to $17.6M Entrepreneur | Sam DeMaio Startup Journey | Episode 69
- Annamarie Davison How a Twenty-Something Entrepreneur Landed 35% Equity | Episode 68
- Chynna Hansenon Mom of 5 Builds Million-Dollar Apparel Brands | Episode 67
- Scott Jensenon Building a National Outdoor Brand from Scratch | Episode 66
- Todd Kuhnon 25 Years in Fitness, 2 Big Exits, Zero Investors | Episode 65
Where to find this show
Audience & reach
Based on observed visual branding, sponsors appear to be B2B service providers and regional financial institutions (e.g., DRGN SLYR, East Idaho Credit Union). The audience of aspiring founders would likely be receptive to marketing services, financial products for small businesses, and productivity software.
Subscriber and view counts are pulled live from YouTube and re-verified on a 30-day cycle. Listener estimates for the RSS feed aren't published here unless they're host-verified.
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People also ask
- What is the host's real name?
- The host's name is Stuart "Stu" Draper.
- Is the Startups With Stu podcast still running?
- Yes, the podcast releases new episodes on a weekly basis.
- What is the show's format?
- It is a long-form interview podcast where host Stu Draper talks with entrepreneurs and investors about their journeys.
- How can I be a guest on the podcast?
- The official podcast website has a contact form for potential guests to get in touch. The show typically features founders and investors who are seeking advice or sharing their stories.
- Where can I listen to the podcast?
- The podcast is available on YouTube, Apple Podcasts, and other major podcast platforms.
Built from the show's public RSS feed, YouTube, the host's own websites, and the cited sources below. Computed and AI-extracted fields are labelled. Facts only — no private info, no fabrication, no transcripts republished.
Sources & how this page was built
This page is AI-assisted, grounded in the public sources cited below, and host-verifiable. We publish facts only; we do not republish transcripts. If anything here is wrong, the host can claim and correct the page above.Model: gemini-2.5-pro · high confidence
- [01]Host Stuart Draper | About the Podcaststartupswithstu.com
- [02]Podcast Episodes | Startups with Stustartupswithstu.com
- [03]Stuart Draper — Founder & CEO, Stukent.com | Evelyn Learningevelynlearning.com
- [04]Stuart Draper - Founder and CEO of Stukent.com - IdeaMenschideamensch.com
- [05]Digital Marketing Essentials by Jeff Larson and Stuart Drapergoodreads.com
- [06]Be a Guest on the Show | Startups with Stu Podcaststartupswithstu.com
- [07]Stuart Draper, Author at Inc.inc.com
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