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Craig Hewitt Podcasts
No need for alarm! We're Pros here.
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A bootstrapped business mastermind with Craig Hewitt and Ken Wallace
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We believe that everyone has the potential to achieve greatness, and that the key to unlocking this potential is through personal development. Our podcasts are designed to help you cultivate the skills and mindset you need to achieve your goals and live the life you want.
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The original podcast for bootstrapped and mostly bootstrapped startups, this show follow the stories of founders as they start, acquire, and grow SaaS companies. Hear when they fail, struggle, succeed, and take you with them through the tumultuous life of a SaaS founder. If you like Mixergy, This Week in Startups, or SaaStr, you’ll enjoy Startup for the Rest of Us.
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My name is Tiago and I am a full time Indie Maker. I build startups without any external investment and my goal is to perfect my entrepreneurial craft and reach $100K ARR (Annual Recurrent Revenue) Join me as I narrate my story and interview other entrepreneurs. Join our community
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Podcraft is your weekly, no-nonsense guide to honing the art of podcasting, hosted by veteran creators Colin and Matthew. With over 30 years of combined experience, they cover everything from choosing the right mic to growing your audience and making money from your show. Some episodes dive deep into one topic, like titling episodes or using live events to build your brand, while others feature real-life case studies from podcasters who've been there and done it. Whether you're just starting ...
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"Be Who You Want To Be" is a new series of conversations with Kristen Hewitt, an Emmy-Award winning South Florida Television Reporter, host, writer, and mom of two. Each episode features a fun and candid discussion with people who are living their best, and most authentic lives. The goal is to learn about their journey, share their message, and inspire others to be who they truly want to be.
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Exploring the practical and exciting alternate realities that can be unleashed through cloud driven transformation and cloud native living and working. Each episode, our hosts Dave, Esmee & Rob talk to Cloud leaders and practitioners to understand how previously untapped business value can be released, how to deal with the challenges and risks that come with bold ventures and how does human experience factor into all of this? They cover Intelligent Industry, Customer Experience, Sustainabili ...
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BeTempered Episode 83 - Building a Practice on Gratitude and Trust with Dr. Craig Hewitt
1:47:07
1:47:07
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1:47:07What if the hardest detours in life turn out to be the exact preparation you needed for a purpose you didn’t see coming? Dan Schmidt and Ben Spahr sit down with Dr. Craig Hewitt, a husband, father of five, and Navy trained dentist whose path runs from a small Catholic school to Parris Island, to Hawaii, and then back home to build a practice anchor…
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Episode 809 | What I Learned Diving into A.I. for 100 Days (with Craig Hewitt)
39:31
39:31
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39:31What are the can't-miss AI tools for SaaS founders? In this episode, Rob Walling sits down with Craig Hewitt, founder of Castos, to dive deep into Craig’s “100 Days of AI” YouTube series. They discuss the lessons learned from exploring the latest AI tools for founders, why ChatGPT might not be the best option for SaaS entrepreneurs, and which AI pl…
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BeTempered Episode 85 - Coaching for More Than the Scoreboard with Tyler Luce
1:29:20
1:29:20
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1:29:20What does it look like to coach for something bigger than a scoreboard? In this episode of BeTempered, hosts Dan Schmidt and Ben Spahr sit down with Tyler Luce, a sixth grade social studies teacher and head varsity baseball coach at National Trail, to talk about leadership that lasts longer than a season. Tyler’s story begins in a blue collar home …
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CR118: Christmas special! Return to the simulation with Anders Indset, Author & Philosopher
1:30:13
1:30:13
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1:30:13From all of us at Cloud Realities, MERRY CHRISTMAS!!!! Back in our December 2022 Christmas special, we explored the far reaches of reality, asking whether we live in a simulation and if that even matters. Now, we return to that question with fresh perspectives and new challenges… In this last Cloud Realities podcast of 2025, Dave, Esmee and Rob ret…
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#386 - Why I Spent $1,500 on a Domain for My SaaS
19:04
19:04
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19:04I share why I bought my most expensive domain ever for $1,500 and break down the strategy behind it. I talk about the shift from product development to mastering distribution, especially through SEO. I discuss the difference between active and passive distribution and why owning the right keyword domains can give a huge advantage. I reveal our plan…
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After funding 210+ B2B SaaS companies, what patterns have emerged? In this episode, Rob Walling shares the 2025 State of TinySeed, from its first fund in 2018 to a global portfolio of over 210 B2B SaaS companies. He reflects on TinySeed’s growth, what the data reveals about today’s founders, funding trends, and the rise of AI-first startups. Topics…
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Protecting Your Creative Brain in the Age of AI
44:37
44:37
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44:37Are you using AI to sharpen your thinking, or quietly letting it replace it? Can podcasters and creators still work with AI without losing the slow, human thinking that makes ideas worth sharing? We talk about using AI as a sounding board rather than a generator, why “thinking walks” still matter, and how convenience can flatten creativity if you a…
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BeTempered Episode 84 - 2025 The Year That Clarified Our Mission
50:46
50:46
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50:46Before Christmas rushes past, we press pause to ask better questions. What truly mattered this year? Where is God leading the mission of BeTempered? And how do we show up for people in ways that outlast trends, algorithms, and noise? Hosts Dan Schmidt and Ben Spahr reflect on a season of growth, clarity, and calling, and they officially welcome the…
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CRSP08: State of AI 2025 pt.3: AI Unplugged - from data to sovereign intelligence with Johanna Hutchinson, BAE Systems
42:58
42:58
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42:58In this last episode of the special AI mini-series, we now explore the human side of transformation, where technology meets purpose and people remain at the center. From future jobs and critical thinking to working with C-level leaders, how human intervention and high-quality data drive success in an AI-powered world. This week Dave, Esmee , Rob si…
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Episode 811 | When to Delegate the "Core Four SaaS Skills," Freemium Retention Rates, and More Listener Questions (A Rob Solo Adventure)
34:15
34:15
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34:15How do you step back from daily decisions without losing control of your SaaS? In this episode, Rob Walling answers listener questions about when to delegate key founder skills, whether great founders can succeed with any idea, and the limits of no-code or “vibe-coded” apps. To help answer one question, he calls up Ruben Gamez to get his insights o…
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#367 - We Just Moved In To Our Own Office
24:43
24:43
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24:43I share the story behind getting our first dedicated Podsqueeze office in Portugal. I talk about the challenges of moving from a co-working space, hunting for a budget-friendly place, and doing DIY renovations with my co-founder. I explain how we furnished the space cheaply, set up a gym and podcast studio, and optimized for productivity. I cover o…
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Flat Downloads Don’t Always Mean Flat Growth. But They Might Hide a Bigger Problem
40:12
40:12
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40:12Imagine a podcaster who has been publishing for a couple of years. Every time they check their stats, the number is the same. They assume they have hit a plateau. So they spend more on marketing. They push harder on promotion. Nothing changes. The number stays flat. What that number does not show is what is happening underneath. New listeners are f…
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CR117 Redesigning industries with AI with Scott Hanselman, Microsoft
48:57
48:57
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48:57AI is transforming software development—redefining roles, creativity, and community, while challenging developers to embrace ambiguity, orchestrate specialized agents, and stay human through empathy and curiosity. Will AI make developers more creative, or will we forget how the machine really works under the hood? This week Dave, Esmee , Rob sit do…
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Episode 810 | The Best A.I. Coding Stack, Shipping Fast, and More Listener Questions (With Derrick Reimer)
53:41
53:41
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53:41How much design polish is really enough? In this episode, Rob Walling is joined by fan favorite Derrick Reimer for a new round of listener questions. They dig into the best AI coding stacks right now, how to ship fast without losing polish, whether AI is changing the kind of risk founders face, and when to start taking security seriously. Episode S…
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Growth Tips for Stalling Audiences and Narrative Lessons for Non Fiction Podcasts
44:20
44:20
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44:20Fiction podcasts often hold listeners for longer than non-fiction shows. But what can non-fiction creators learn from this? We break down the simple storytelling tools that keep audiences hooked, including open loops, stronger intros, clearer arcs, and themed seasons. We also highlight some easy wins that improve retention, such as smoother transit…
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CRLIVE58 AWS re:Invent 2025: European Digital Sovereign Futures with Mustafa Isik, AWS + Team reflections on re:Invent 2025
1:13:02
1:13:02
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1:13:02Live from the iconic Venetian in Las Vegas, we’re rolling out an exclusive mini-series dedicated to AWS re:Invent 2025! Tune in as we sit down with AWS visionaries and take the pulse of the industry on everything shaping the future, Cloud innovation, GenAI, Agents, and the hottest trends making waves. And because what happens in Vegas doesn’t alway…
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CRLIVE57 AWS re:Invent 2025: Financial Renovation with Scott Mullins, AWS
30:38
30:38
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30:38Live from the iconic Venetian in Las Vegas, we’re rolling out an exclusive mini-series dedicated to AWS re:Invent 2025! Tune in as we sit down with AWS visionaries and take the pulse of the industry on everything shaping the future, Cloud innovation, GenAI, Agents, and the hottest trends making waves. And because what happens in Vegas doesn’t alway…
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BeTempered Episode 82 - Inside the Support Systems That Change a Child’s Trajectory with Allie Shafer
1:24:20
1:24:20
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1:24:20What happens when a child cannot focus in class because the lights were shut off at home, there is no food in the cupboard, or their clothes have not been washed in a week. On this episode of BeTempered, hosts Dan Schmidt and Ben Spahr sit down with Eaton Community Schools Success Liaison Allie Shafer to shine a light on the non academic barriers t…
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CRLIVE56 AWS re:Invent 2025: Driving Innovation in Automotive and Energy & Utilities with Rob Boetticher and Howard Gefen, AWS
55:04
55:04
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55:04Live from the iconic Venetian in Las Vegas, we’re rolling out an exclusive mini-series dedicated to AWS re:Invent 2025! Tune in as we sit down with AWS visionaries and take the pulse of the industry on everything shaping the future, Cloud innovation, GenAI, Agents, and the hottest trends making waves. And because what happens in Vegas doesn’t alway…
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CRLIVE55 AWS re:Invent 2025: re:Accelerating Europe with Tanuja Randery, AWS
34:31
34:31
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34:31Live from the iconic Venetian in Las Vegas, we’re rolling out an exclusive mini-series dedicated to AWS re:Invent 2025! Tune in as we sit down with AWS visionaries and take the pulse of the industry on everything shaping the future, Cloud innovation, GenAI, Agents, and the hottest trends making waves. And because what happens in Vegas doesn’t alway…
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CRLIVE54 AWS re:Invent 2025: Making it real in Industries with Tim Murnin, AWS
31:15
31:15
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31:15Live from the iconic Venetian in Las Vegas, we’re rolling out an exclusive mini-series dedicated to AWS re:Invent 2025! Tune in as we sit down with AWS visionaries and take the pulse of the industry on everything shaping the future, Cloud innovation, GenAI, Agents, and the hottest trends making waves. And because what happens in Vegas doesn’t alway…
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CRLIVE53 AWS re:Invent 2025: Driving Cloud and AI success through collaboration with Chandra Pinapala, AWS
39:28
39:28
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39:28Live from the iconic Venetian in Las Vegas, we’re rolling out an exclusive mini-series dedicated to AWS re:Invent 2025! Tune in as we sit down with AWS visionaries and take the pulse of the industry on everything shaping the future, Cloud innovation, GenAI, Agents, and the hottest trends making waves. And because what happens in Vegas doesn’t alway…
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What’s the Best Way for a Small Podcast to Make Money?
51:55
51:55
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51:55What if monetising a podcast was simpler than the usual laundry list of tactics suggests? A new model called the Three As breaks earning potential into three clear paths: Audience, which includes supporter perks and light ads Authority, which covers coaching, courses, and specialist services Assets, which includes books, products, and affiliate inc…
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BeTempered Episode 81 - 'Small Choices, Big Impact' with Brian Ballenger, Mark Broeker, and the WC Leads Cohort
52:45
52:45
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52:45What makes someone worth following when no one is watching. In this leadership roundtable, that question sits in the center of the table as stories unfold from classrooms, locker rooms, offices, and quiet early mornings when no one else is around to see the work. On this episode of BeTempered, hosts Dan Schmidt and Ben Spahr sit down with guests Br…
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CR116: Unlocking Cloud for critical missions with Danny Polaine, Thales
47:45
47:45
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47:45Accelerating cloud adoption to drive innovation across domains like space, identity, and naval systems presents unique challenges. Success depends on aligning organizational culture, governance, financial models, and regulatory frameworks to enable collaboration, scalability, and software-defined capabilities. This week, Dave, Esmee, and Rob speak …
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Episode 808 | A $500k "Step 1" Business, When to Consider SOC2, and More Listener Questions
29:45
29:45
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29:45Is it time to sell, autopilot, or double down on your plateaued SaaS business? In this episode, Rob Walling tackles listener questions and shares practical frameworks for what to do when your product hits a plateau, explains why “autopilot” often leads to decline, and outlines when founders should seriously consider SOC 2 compliance. Rob also talks…
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