Best Startupstrategies Podcasts (2025)

1
How to Fire Someone: A Business Owner’s Guide to Tough Conversations 46:57

2d ago46:57

46:57

Firing someone is one of the hardest parts of leadership—but avoiding it can cost your business even more. In this episode of Build Your Business, Matt and Chris Reynolds break down how to fire someone the right way: with clarity, compassion, and professionalism. Whether it's your first time or you're trying to improve your process, you'll learn ho…

1
#363 - Sunil Patel, CEO of Tekmetric on ignoring customer wishlists to kill industry dinosaurs 41:40

4d ago41:40

41:40

This podcast interview reveals why the best software breaks all the rules. My guest is Sunil Patel, CEO of Tekmetric. Before building software, Sunil owned and operated multiple auto repair shops, giving him a rare insider's perspective on the industry's real problems. He's a practical entrepreneur who's obsessed with simplicity and hates wasted ef…

1
Effective Delegation for Perfectionists: How to Let Go Without Lowering Standards 42:09

9d ago42:09

42:09

📄 Are you stuck doing everything yourself because no one else can do it “right”? In this episode of Build Your Business, Matt and Chris Reynolds break down why perfectionists struggle with delegation—and how to fix it. Learn how to build trust, communicate expectations clearly, and use systems that protect your standards without burning you out. Di…

1
#362 – How Sharat Potharaju built a 50,000-customer business by saying "no" to endless opportunities 45:38

11d ago45:38

45:38

This podcast interview focuses on the entrepreneurial journey to discovering powerful strategic frameworks through trial and error. My guest is Sharat Potharaju, CEO of Unicode. Sharat is a serial entrepreneur with 15 years of experience. He navigated through a decade of ventures that didn't scale before founding Uniqode in 2019. His company has si…

1
When Important Becomes Urgent: How to Prioritize What Actually Matters 28:32

16d ago28:32

28:32

As a business owner, it's easy to push off the things that really matter—your family, your health, your strategic thinking—because they're not screaming for attention. But eventually, they will become urgent. In this episode, Matt Reynolds shares how he cleared his schedule, tackled long-neglected priorities, and rediscovered what it means to lead …

1
#361 - Imran Syed, CEO of Hatchproof on building companies through deep problem understanding, not solutions 51:32

18d ago51:32

51:32

This podcast interview focuses on the entrepreneurial journey of finding purpose and transformation through failure. My guest is Imran Syed, CEO of Hatchproof. After leading a high eight-figure exit at Instapage as COO, Imran witnessed how misalignment among leadership destroyed tens of millions in enterprise value during a failed product launch. I…

1
Take Some Time Off: How Rest Makes You a Better Leader 19:12

23d ago19:12

19:12

In this episode, Matt Reynolds shares why learning to take some time off might be the smartest thing you do as a business owner. He unpacks how intentional rest can increase creativity, sharpen your strategic thinking, and actually improve your output as a leader. Whether it’s a simple weekend away or a longer retreat, Matt offers practical steps f…

1
#360 - Zach Wasserman, Co-founder of Fleet on community-driven business growth 52:51

25d ago52:51

52:51

This podcast interview focuses on the entrepreneurial journey of turning transparency into business advantage. My guest is Zach Wasserman, Cofounder and Tech Evangelist of Fleet. With over a decade of experience in open source software development, Zach helped create the widely-adopted OSquery project at Facebook in 2014, which has since become an …

1
Pivoting for Growth: How Founders Spot Opportunities and Adapt 43:18

1M ago43:18

43:18

How do you know when it’s time to pivot—and how do you pivot without blowing everything up? 🚀Matt and Chris Reynolds break down real-world strategies for spotting opportunity, adapting to market shifts, and making founder pivots that fuel real business growth. Whether you’re navigating slow sales, customer churn, or big market changes (like AI!), t…

1
#359 - Jan Bruce, CEO of meQuilibrium on when to ignore the capital temptation 47:30

1M ago47:30

47:30

This podcast interview focuses on what it takes to build a successful software company by following your convictions even when easier paths tempt you. My guest is Jan Bruce, CEO of meQuilibrium (MeQ). In 2011, after years in the media industry during its technological disruption, Jan witnessed firsthand how stress and resistance to change were deva…

1
Embracing Remote Work: How Founders Build Freedom & Output 33:33

1M ago33:33

33:33

In this episode of Build Your Business: From Fear to Freedom, Matt Reynolds and Chris Reynolds dive deep into the powerful benefits of embracing remote work—and why they’ll never return to a traditional office setup. From unlocking personal freedom to building high-performing teams across time zones, remote work isn’t just a lifestyle change—it’s a…

1
#358 - Samuel Logan, CEO of Evidencity on when slowing down accelerates growth 50:39

1M ago50:39

50:39

This podcast interview focuses on the entrepreneurial wisdom gained through building a data-driven business from scratch. My guest is Samuel Logan, Founder and CEO of Evidencity. After bootstrapping Evidencity as his fourth venture, Samuel Logan has spent a decade building a company with a profound mission: creating transparency to eliminate modern…

1
The Power of Thinking Time to Unlock Founder Potential 37:20

1M ago37:20

37:20

Quiet reflection might be the most powerful leadership tool you're not using. In this episode of Build Your Business, Matt and Chris explore how "thinking time" fuels strategic clarity, innovation, and sustainable leadership. Unlocking Founder Potential Starts with Thinking Time Intentional solitude creates space to lead, not just operate. Thinking…

1
#357 - Rich Kahn, Founder and CEO of Anura on transforming a reluctant side project into a viable business 1:00:01

2M ago1:00:01

1:00:01

This podcast interview focuses on entrepreneurial decision-making and product development. My guest is Rich Kahn, CEO of Anura. Rich has been building tech companies since 1993. In 2003, while running an ad network with his wife, clients began complaining about traffic quality issues. When he discovered no commercial fraud detection solutions exist…

1
Overcoming Founder Isolation: Break the Cycle of Overwork & Anxiety 41:29

2M ago41:29

41:29

Feeling like you’re carrying the entire business on your shoulders? You’re not alone. In this vulnerable episode of Build Your Business, Matt and Chris talk openly about the emotional weight of being a founder—and how to break free from the loop of overwork, anxiety, and isolation. 1. What Founder Isolation Really Feels Like More than being alone—i…

1
The Art of Sales Without the "Sales Tactics" 58:17

2M ago58:17

58:17

Sales doesn't have to feel sleazy or scripted. In this episode of Build Your Business, Matt and Chris Reynolds explore how to master the art of sales by being authentic, problem-focused, and client-centered. The Power of Authenticity in Sales The best salespeople lead with honesty and care. Build trust through real, meaningful conversations. Focus …

1
#356 - Geordy Murphy, Fobesoft on building resilience through market downturns 51:12

2M ago51:12

51:12

This podcast interview focuses on building remarkable software that creates sustainable competitive advantage. My guest is Geordy Murphy, CEO of Fobesoft. After three decades as a successful restaurateur who owned one of San Francisco's top four restaurants, Geordy sold his business and relocated to Florida. Despite having no software background, h…

1
#355 - Maximus Greenwald, Warmly on Mastering the Pivot Journey 45:36

2M ago45:36

45:36

This podcast interview focuses on the entrepreneurial journey of persistence and adaptation. My guest is Maximus Greenwald, CEO of Warmly. After working at Google, Max and his co-founders quit their jobs to start a company with what he calls "the world's worst idea" - Tinder for co-founders. What makes his journey fascinating is how he navigated th…

1
#354 - Ash Didwania, Workzone on Achieving Growth Without Sacrificing Profitability 57:47

2M ago57:47

57:47

This podcast interview focuses on the entrepreneurial challenge of revitalizing a 20-year-old SaaS business in a market with hundreds of competitors. My guest is Ash Didwania, CEO of Workzone. Ash took the helm of Workzone in December 2023 after the company was acquired by Big Band Software. Despite being profitable with a sticky customer base (7-y…

1
#353 - Krishna Raj Raja, CEO SupportLogic - Why investor skepticism can signal your biggest opportunity 49:30

3M ago49:30

49:30

This podcast interview focuses on transforming how B2B companies leverage customer interactions for growth. My guest is Krishna Raj Raja, CEO of SupportLogic. From his early days as one of VMware's first support engineers, Krishna discovered something the industry had missed - the most valuable customer insights were being lost in departmental silo…

1
#352 - David DeWolf, CEO of Knownwell on when NOT to scale 54:44

3M ago54:44

54:44

This podcast interview focuses on the critical decisions that define successful scaling. My guest is David DeWolf, CEO of Knownwell. After growing Three Pillar Global to 2000 employees across nine countries, David learned that sometimes the best way to scale is to deliberately slow down. During COVID, he made the bold choice to retain all employees…

1
#351 - Nick Wassenberg, Cludo on customer-driven growth strategy 50:22

3M ago50:22

50:22

A story about transforming a horizontal solution into targeted value propositions This podcast interview focuses on the entrepreneurial journey to build sustainable growth by deeply understanding customer needs over chasing broad market opportunities. My guest is Nick Wassenberg, CEO of Cludo. Nick is a marketing veteran turned CEO with an entrepre…

1
#350 - Smadar Tadmor, Claro Mentor on Starting from Zero at the Top 55:15

3M ago55:15

55:15

This podcast interview focuses on the entrepreneurial journey to make effective leadership development available for everyone. My guest is Smadar Tadmor, CEO of Claro Mentor. Smadar Tadmor is a visionary leader who's on a mission to change the way organizations develop their managers. With over 30 years in HR and organizational development, she fou…

1
#349 - Robbert Lodewijks on turning validation into velocity 41:00

4M ago41:00

41:00

This podcast interview focuses on the entrepreneurial journey to transform thoughtful validation of the problem into confident scaling of his SaaS business. My guest is Robbert Lodewijks, Co-founder and CEO of Hulo AI. Robbert Lodewijks is an entrepreneur who understands the delicate balance between patience and ambition. His journey began with a p…

1
#348 - Marco Benitez, CEO of Rook - on transforming health data into enterprise value. 49:44

4M ago49:44

49:44

This podcast interview focuses on the entrepreneurial journey to transform messy wearable data into standardized enterprise gold. My guest is Marco Benitez, CEO of Rook. Marco is a tech entrepreneur on a mission. He's a former Tae Kwon Do champion who transformed his athletic discipline into entrepreneurial success. At just 22 years old (while stil…

1
#347 - Mark Fershteyn, CEO, Recapped - on transforming complex B2B sales 45:38

4M ago45:38

45:38

This podcast interview focuses on the entrepreneurial journey to make buying and selling in B2B remarkably easier. My guest is Mark Fershteyn, Founder and CEO of Recapped. Mark is a tech entrepreneur on a mission. He has a passion for building things from scratch. He specifically prefers going from "zero to one" rather than maintaining existing sys…

1
#346 - Randy Wootton, CEO of Maxio - on strategic growth through integration 45:35

4M ago45:35

45:35

This podcast interview focuses on the entrepreneurial journey to successfully merge and integrate two distinct SaaS companies while balancing stakeholder interests, maintaining growth, and navigating complex market dynamics. My guest is Randy Wootton, CEO of Maxio. Randy is a serial CEO. Before becoming CEO, he held senior positions at industry gia…

1
#345 - Evan Huck, CEO of UserEvidence - on customer evidence democratization. 55:21

5M ago55:21

55:21

This podcast interview focuses on the entrepreneurial journey to democratize customer evidence and change the way B2B software buying decisions are made. My guest is Evan Huck, Co-founder and CEO of UserEvidence. Evan's journey in the tech industry is a testament to his entrepreneurial spirit and sales acumen. He started his career as an SDR (Sales…

1
#344 - Wes Bush, Founder of Productled.com - on product-led business transformation 46:26

5M ago46:26

46:26

This podcast interview focuses on the challenges and strategies of implementing product-led growth (PLG) effectively (and when to stay out of PLG). My guest is Wes Bush, product-led growth pioneer, founder of Productled.com, and bestselling author. Wes is widely recognized as one of the pioneers of the product-led growth movement, challenging an en…

1
#343 - Aytekin Tank, CEO Jotform - on continuous innovation and momentum 58:45

6M ago58:45

58:45

This podcast interview focuses on the entrepreneurial journey to build a global SaaS company with 25 million users without venture funding. My guest is Aytekin Tank, Founder and CEO of Jotform. Aytekin founded Jotform in 2006, creating a pioneering WYSIWYG online form builder that has grown to serve over 25 million users worldwide today. What's rem…

1
#342 - Ozan Unlu, CEO of Edge Delta - on solving critical business problems. 51:22

6M ago51:22

51:22

This podcast interview focuses on the entrepreneurial journey to eliminate the risk that cost businesses thousands of $ per second of downtime. My guest is Ozan Unlu, Founder and CEO of Edge Delta. Ozan has had an unconventional career path that spans multiple disciplines. He started as a nanoscientist and researcher before transitioning into the t…

1
#341 - Daniel Saks, CEO of Landbase - on reclaiming your day with AI 57:08

6M ago57:08

57:08

This podcast interview focuses on the entrepreneurial journey to redefine software's role from engagement-driven to impact-driven solutions. My guest is Daniel Saks, CEO of Landbase. Daniel's entrepreneurial journey has deep roots in a 100-year-old family business. He grew up in Niagara Falls, Canada, where his family owned a furniture store founde…

1
#340 - Mark Kosoglow, CEO of Operator - on critical thinking in sales 42:21

6M ago42:21

42:21

This podcast interview focuses on the entrepreneurial journey to transform toxic sales automation. My guest is Mark Kosoglow, CEO of Operator. Mark is a tech entrepreneur on a mission. A big mission. He's a sales expert who played a crucial role in helping scale Outreach from zero to over $230 million in revenue in just 8-years. Being part of the r…

1
#339 - Griffin Parry, CEO of m3ter - on taking the pain out of billing operations. 50:22

6M ago50:22

50:22

This podcast interview focuses on the entrepreneurial journey to build mission-critical billing infrastructure for complex B2B SaaS pricing models. My guest is Griffin Parry, Founder and CEO of m3ter. Griffin Parry is a serial Entrepreneur. In 2013, he founded GameSparks, a backend-as-a-service platform for video games, which he sold to Amazon in 2…

1
#338 - Hadassah Backman, CEO of Guardoc Health - solving critical industry problems 48:01

7M ago48:01

48:01

This podcast interview focuses on the entrepreneurial journey to change the way healthcare nurses can work to improve patient safety. My guest is Hadassah Backman, CEO of Guardoc Health. Hadassah has nursing roots: She started her career as a registered nurse and has built hands-on experience in emergency room and hospice care. This clinical backgr…

1
#337 - Dan Uyemura, CEO of Pushpress - on Vertical SaaS differentiation 47:45

7M ago47:45

47:45

This podcast interview focuses on the entrepreneurial journey to build deep vertical business solutions that deliver 10x value for every 1x in price charged. My guest is Dan Uyemura, CEO of Pushpress. Dan has had an entrepreneurial spirit from a young age. He was a Dot-com era pioneer: During college, he founded Mixture.com, a platform that was ahe…

1
#336 - Victor Kristof, CEO of DemoSquare - on resilient customer-driven innovation. 42:39

7M ago42:39

42:39

This podcast interview focuses on the entrepreneurial journey to democratize political data and anticipate regulatory changes. My guest is Victor Kristof, Co-founder and CEO of DemoSquare. Victor is a fascinating individual with a unique blend of academic excellence, entrepreneurial spirit, and a passion for leveraging technology to enhance democra…

1
#335 - Joaquim Lecha, CEO of Typeform - on creating SaaS products customers love. 55:13

7M ago55:13

55:13

This podcast interview focuses on the entrepreneurial journey to help all of us to have conversations that drive action and meaningful connections. My guest is Joaquim Lecha, CEO of Typeform. Joaquim (Kim) is a tech entrepreneur on a big mission, bringing over 20 years of experience in high-growth companies. He started his career in M&A, strategy, …

1
#2 - Overthrowing the Tyranny of the Urgent (Legacy Episode) 17:24

8M ago17:24

17:24

Matt and Chris Reynolds discuss the concept of the urgent versus the important, and the four quadrants into which you can divide all work and chores: Not urgent, not important Urgent, not important Urgent and important Not urgent, but important Most people spend their time in the first three quadrants of the urgency/importance spectrum, leaving lit…

1
#334 - Bridget Harris, CEO of You Can Book Me - on the art of Bootstrapping. 46:18

8M ago46:18

46:18

This podcast interview focuses on the entrepreneurial journey to build a successful bootstrapped SaaS company in the highly competitive scheduling software market. My guest is Bridget Harris, Co-founder and CEO of You Can Book Me. Bridget has had three distinct careers, showcasing her versatility and adaptability: She started in the television and …

1
#333 - Caitlin MacGregor, CEO of Plum- on successfully navigating market change 56:28

8M ago56:28

56:28

This podcast interview focuses on the entrepreneurial journey from the last 5 years to turn Plum into the best Talent Intelligence solution on the market. My guest is Caitlin MacGregor, Co-Founder and CEO of Plum Caitlin MacGregor co-founded Plum in 2012 and has been an earlier guest on my podcast (#54 in February 2019). She was voted "most likely …

1
#332 - Matt Van Itallie, CEO of Sema - on executive Insight into code quality. 50:22

8M ago50:22

50:22

This podcast interview focuses on the entrepreneurial journey to make complex code understandable for business leaders. My guest is Matt Van Itallie, Founder and CEO of Sema. Matt has a diverse background spanning law, consulting, education, and tech, and he has held leadership roles at edtech and govtech companies like Social Solutions, and People…

1
#331 - Christian Klepp, host of the “B2B Marketers on a Mission” Podcast - on how curiosity drives B2B marketing. 45:34

8M ago45:34

45:34

This podcast interview focuses on the entrepreneurial journey to drive change and adapt as a B2B marketer in an evolving business landscape. My guest is Christian Klepp, Co-Founder of EINBLICK Consulting and Host of the B2B Marketers on a Mission podcast. Christian is a global citizen, entrepreneur, podcast host, and B2B branding expert with over 1…

1
#330 - Thomas Wulff Wilhelmsen, CEO of Less - on creating a customer-funded business. 47:11

9M ago47:11

47:11

This podcast interview focuses on the entrepreneurial journey to empower business users, especially in SMEs, to easily find insights in their data without technical complexities. My guest is Thomas Wulff Wilhelmsen, Co-founder and CEO of Less. Thomas and his co-founder Daniel previously worked as consultants in the data space before founding Less. …

1
#329 - Angelo Coletta, CEO of Zakeke - on becoming a global leader in visual commerce. 48:54

9M ago48:54

48:54

This podcast interview focuses on the entrepreneurial journey in identifying an emerging opportunity and building an innovative, fast-growing company that transforms how we shop online. My guest is Angelo Coletta, CEO and Co-founder of Zakeke. Angelo is a serial entrepreneur who has founded and exited multiple companies. In 2017 he co-founded Zakek…

1
#328 - Matthew McGrory, CEO at Arwen AI, on solving a problem of global scale. 59:34

9M ago59:34

59:34

This podcast interview focuses on the entrepreneurial journey to make social a positive place again - for everyone. My guest is Matthew McGrory, CEO of Arwen AI. Matthew is a tech- entrepreneur on a big mission. He has held tech leadership roles: IT Director at Logicalis, Director Managed Services at Acora, and Managing Director at Carrenza (a clou…

1
#327 - Josh Ellars, CEO of OpenGTM - on Differentiation and growing efficiently. 47:18

9M ago47:18

47:18

This podcast interview focuses on the entrepreneurial journey to take GTM efficiency to the next level for enterprise SaaS companies. My guest is Josh Ellars, CEO of OpenGTM. Josh has over 15 years of experience leading successful go-to-market (GTM) functions at high-growth SaaS companies like Metalogix, Qualtrics, and OpenGov. This extensive backg…

1
#326 - Niklas Hanitsch, CEO of SECJUR - on balancing culture and growth challenges 45:30

9M ago45:30

45:30

#326 - Niklas Hanitsch, CEO of SECJUR - on balancing culture and growth challenges A story about maintaining a blue ocean market in the rapidly evolving compliance automation landscape. This podcast interview focuses on the entrepreneurial journey to sustain in a heavily competitive market. My guest is Niklas Hanitsch, Co-founder and CEO of SECJUR.…

1
#325 - Matt Achariam, Co-CEO Clay - on fueling organic growth through Remarkability. 38:59

10M ago38:59

38:59

This podcast interview focuses on the entrepreneurial journey to finally solve the problem of managing all your personal and professional relationships. My guest is Matt Achariam, Co-Founder and Co-CEO of Clay. Matt has a diverse background in product development and design. He was a principal at design agency FortySix, working with clients like Di…

1
#324 - Lee Rubin, Founder and CEO of Confetti - on designing for business resilience. 43:55

10M ago43:55

43:55

This podcast interview focuses on the entrepreneurial journey to build a business that can survive crises and emerge stronger every time. My guest is Lee Rubin, founder and CEO of Confetti. Lee is a visionary culture leader with over a decade of experience in B2B sales. In 2014 she founded Wekudo - a remote corporate event planning agency. The idea…

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Startupstrategies Podcasts

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