Quick, actionable episodes for aspiring SaaS founders who want to build on their own terms. No fluff, no theory, just real strategies from a serial bootstrapper who's done it multiple times.
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Unpacking innovative technologies and business trends, forecasting on what’s hip and set to takeover Africa and the globe in general. We also chat with upcoming disrupters and showcase their innovations.
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We help entrepreneurs scale their business with remote teams. In every episode we deliver effective solutions for the challenges business owners and executives face, with experienced guests and practical answers to solve real issues. Hosts Gwenn and Jeremy Aspen have helped hundreds of businesses scale their growth, as the modern workplace isn't constrained by walls of a building and remote teams work to scale your business fast. https://anequim.net/property-management-bootstrappers/
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There’s no doubt that Silicon Valley is THE place for entrepreneurs. Some people choose to grow with external funding, and some choose to self-fund, and they are often called bootstrapper. According to statistics, only 0.4% of all U.S. companies grow past $10 Million in revenue. In this series of interviews, I’m talking to local bootstrappers who have pushed their businesses into that top 0.4%. My hope is that their experiences can inspire others to make a difference in this valley. To read ...
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Welcome to the "Underdogs Bootstrappers Gamechangers" podcast, where we celebrate the relentless spirit of those who defy the odds, challenge the status quo, and make a lasting impact in their fields. Join us as we dive into the inspiring stories and strategies of bootstrappers, underdogs, and gamechangers from various industries. In each episode, we'll explore the remarkable journeys of individuals who have built their success from the ground up. From starting with limited resources to over ...
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There's a ton of talk about AI related to software dev, but what about user research? What AI tools and strategies can we leverage to level up our game here? Free Email Course - https://bootstrappersparadise.com/course Online Community - https://bootstrappersparadise.com/community Bootstrapper's Paradise - https://bootstrappersparadise.com/…
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Should you build your next app with a no-code solution or via custom development? Let's discuss. Free Email Course - https://bootstrappersparadise.com/course Online Community - https://bootstrappersparadise.com/community Bootstrapper's Paradise - https://bootstrappersparadise.com/Por Sean Boyce
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Here's what I'm building with as of Dec 2025. Lovable - https://lovable.dev/ Cursor - https://www.cursor.com Claude Code - https://claude.ai/ (Sonnet/Ops 4.5) Vercel - https://vercel.com/ Railway - https://railway.com/ Supabase - https://supabase.com/ Free Email Course - https://bootstrappersparadise.com/course Online Community - https://bootstrapp…
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Has UI Design Work Been Made Obsolete By AI?
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5:32Has design work been made obsolete by tools like lovable? Lovable - https://lovable.dev/ Free Email Course - https://bootstrappersparadise.com/course Online Community - https://bootstrappersparadise.com/community Bootstrapper's Paradise - https://bootstrappersparadise.com/Por Sean Boyce
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Does AI Help or Hurt Chances of SaaS Success?
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4:40Does AI make it easier or harder to succeed in building a successful (keyword) SaaS business today? Free Email Course - https://bootstrappersparadise.com/course Online Community - https://bootstrappersparadise.com/community Bootstrapper's Paradise - https://bootstrappersparadise.com/Por Sean Boyce
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New name. New format. Bootstrapper's Paradise is a daily show about building SaaS without investors or even having to code. Five minutes, one actionable idea, every episode. Let's build. Free Email Course - https://bootstrappersparadise.com/course Online Community - https://bootstrappersparadise.com/community Bootstrapper's Paradise - https://boots…
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Send us a text Norman Towns on Outworking the Odds Let’s be real, success isn’t sexy at the start. Norman Towns knows that better than anyone. Before he hit the screen, he was doing all the jobs no one brags about: spinning signs on the sidewalk, washing dishes, pulling overnight security shifts. Whatever it took. In this episode, Norman keeps it r…
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How to Start a Business (Even If You're Scared Sh*tless)
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7:57Send us a text Starting a small business from scratch? Learn how to launch with no money, no connections, no fluff. Ever feel like most business advice is just recycled guru nonsense or comes from people born wealthy? This episode is for the real ones—those starting small businesses without money, privilege, or fancy degrees. This episode kicks off…
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NO CASH, NO PROBLEM: HOW TO HUSTLE YOUR WAY TO THE TOP
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1:17:27Send us a text What does it really take to go from struggling to thriving? In this raw and motivating episode, e-commerce expert Zoe Khan shares her incredible journey from financial desperation to running a successful agency with over 100 employees. Zoe’s story starts with selling plasma just to afford a phone to apply for jobs. Juggling multiple …
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Foster Care Crisis: 80% of Death Row Inmates & 60% of Traffic Victims — A Call for Reform
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55:35Send us a text Foster care crisis, systemic neglect, shocking statistics, death row, traffic fatalities, urgent reform, social justice. Lisa’s journey is a testament to resilience and the power to create change. After enduring 36 foster homes and facing homelessness at 18, she refuses to let the system’s failures define her future. Now, she’s takin…
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Tech-to-CEO Journey & the High-Touch SaaS Model
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26:06Dive into the world of high-touch SaaS with Vee24's CEO, Tomer Azenkot. From tech roles to CEO insights, explore how close customer interaction propels company success. Uncover the power of video chat in elevating the buying experience and why focusing your market strategy reaps rewards. Join us for a masterclass in customer-centric growth. Here ar…
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ENTREPRENEURS: CAN FITNESS GIVE YOU THE EDGE? DR. SHELL HAS THE ANSWER!
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1:01:20Send us a text Want to build a thriving business? Start with your body. In this powerhouse episode, Dr. Shell—doctor, entrepreneur, and Bare Knuckle Fighting Championship competitor—shares how strength training and mental resilience give entrepreneurs the edge they need to win in business and life. Discover why fitness isn’t just about looking good…
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EMPOWERING ENTREPRENEURS TO THRIVE WITH PALOMA
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1:22:16Send us a text Thinking about starting a business but unsure where to begin? We’re here to help. Join us as we explore the key steps to building a strong foundation, featuring insights from Paloma, an experienced business attorney. We’ll break down the importance of choosing the right business structure—like an LLC—to protect your personal assets a…
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IS MONEY BLOCKING YOUR DREAM? HERE’S HOW TO BEGIN! WITH DAVEED BENITO
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1:05:59Send us a text People often focus on all the reasons why they can’t achieve something—lack of money, equipment, or confidence. But what if we flipped the script? Let’s talk about all the ways you can break through those barriers. 💡 We believe this is the moment for independent creators to rise, break the rules, and maybe even reshape the entertainm…
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JUDGE LYNN TOLER: RELATIONSHIPS MAKE OR BREAK SUCCESS
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1:00:57Send us a text Prepare to be inspired by the incredible resilience and wisdom of Judge Lynn Toler, a trailblazer known for her impactful work on "Divorce Court" and "Marriage Boot Camp." We explore the remarkable story of her father, who, despite the odds stacked against him as a black man in a predominantly white industry, supported his family fro…
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Mastering the Art of Event Planning for Business Growth
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15:10What is the true value of an event in today's digital world? The strategic value goes far beyond the execution of the event itself. In this episode, we'll cover the mindset shift event planning requires from the discipline and routine it gives you to the post promotion value in the content you get from it. Learn how events can be a catalyst for bus…
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Marketing Assistance: How VAs Can Transform Your Marketing
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22:21Are you tired of struggling with ineffective marketing tactics for your small business? Look no further! In this episode, Gwenn is joined by marketing expert Matt Tompkins and they dive deep into the world of virtual assistants and how they can transform your marketing. From understanding your ideal customer to simplifying your brand voice, Matt pr…
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The Number One Secret To Project Management
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17:20Are you tired of projects stalling out, underperforming, or causing your team stress? Project management involves a lot of factors, but the key to successful projects happens before you even begin. In this episode, you'll learn the strategy, execution, and people that are the secret to project management. Gwenn and Jeremy have overseen hundreds of …
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Crafting Connections with Heart: The Art of Authentic Networking with DeLo and Sahar
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49:09Send us a text Unlock the secrets to authentic networking in an episode that delves into the heart of true connections. With DeLo's journey from music to insurance as a "connector and protector," and Sahar's passion for empowering small businesses, this discussion is a treasure trove of insights for anyone looking to build relationships with purpos…
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Send us a text Ever wondered how hard work truly pays off? Join me and my friend Gino as we dissect the synergy between effort, strategy, and the elusive concept of success. Our conversation uncovers the transformative power of reading and personal development, especially poignant in times like the COVID era. Gino's journey through books and self-r…
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Email Management: How To Break Free From Your Inbox
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20:51How much time and money are your emails costing you? Checking an average of 121 emails daily costs us time, but the emotional impact can be even more costly. On this episode, Jeremy and Gwen discuss how to deal with the most problematic emails ranging from emails that cause them the most anxiety to the emails that are the most time consuming. Jerem…
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Transforming Work Woes: Channeling Hard Work into Your Ticket to a Brighter Future
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1:00:44Send us a text Ever wonder what it takes to turn a flicker of passion into a blazing career? Essence and Adelaide join us to weave a narrative that begins with a young girl's resolve to transform hairdressing into a business empire, and another's recognition at just 15—a partnership that has since flourished. It's a conversation that celebrates the…
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Scaling Your Business Without Breaking Your Business
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27:51Tired of hitting roadblocks while growing your business? Break free from the cycle of stress with tips on overcoming obstacles like bad emails and outdated sales structures. Join Gwenn & Jeremy as they discuss scaling challenges faced by entrepreneurs. Learn how to navigate people-related drama & optimize recruitment for successful scaling. Scaling…
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The Art of Storytelling in Business Growth and Success with Erin Rogers
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58:23Send us a text Have you ever laughed until you cried or found yourself nodding along to a story that felt like it was plucked from your own life? That's the magic Erin Rogers brings to the table, blending comedy and cinema into storytelling that hits home. On our latest episode of Underdogs, Bootstrappers, Game Changers, we sit down with Erin to di…
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Health And Entrepreneurs: The Solution To Stress
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12:55Are you an entrepreneur who's constantly stressed out? Do you struggle to balance your health and your business? Running a business can take a toll on your health, but it doesn't have to be that way. Join Gwenn and Jeremy as they tackle the critical link between entrepreneurship and health in this episode of Bootstrappers. Gwenn shares a personal s…
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How to Solve The Labor Shortage Crisis For Your Business
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21:14Are you hiring low quality employees? On this episode of Bootstrappers, Jeremy and Gwenn Aspen unveil groundbreaking strategies to navigate the current labor shortage crisis, introducing listeners to the power of remote teams and why you don't have to hire B and C employees to your team. Businesses, now more than ever, are struggling to find qualif…
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Peach Perfect: Cultivating Success at the Roadside Stand with Shannon
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1:01:48Send us a text Have you ever reveled in the simplicity of a roadside fruit stand, the sweet aroma of peaches wafting through the air? Our latest guest, Shannon, a librarian-turned-entrepreneur, guides us through her incredible transformation into the queen of South Carolina's peach stand scene. Her journey, infused with the entrepreneurial spirit, …
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Is Your Customer Service Helping Your Business?
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18:10Is your customer service helping your business? When the quality of your customer service is high, you will keep more clients and they will sell your services better than you can. Discover the power of quality assurance in scaling your business as we unveil three simple yet effective tips that you can start implementing today. In this episode, Gwen…
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Braiding Paths to Success: Essence China's Journey from Underdog to Empire Builder
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1:11:34Send us a text When Essence China started braiding hair in her parents' laundry room, little did she know that she was twining the strands of her future empire. Our latest episode features Essence's journey from humble beginnings to a salon tycoon and beauty school founder, proving how underdogs can bite through systemic barriers with a mix of grit…
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Calendar Management: Intentional Time, Infinite Energy
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20:35Is your calendar working for you or against you? On this episode of the Bootstrappers podcast, Gwen and Jeremy discuss everyone's most precious resource: Their time. Jeremy gives advice on how he structures his work week so you can have a chill Friday. Gwen dives deep on tips and tricks on how to have your assistants save you time. All this and mor…
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Scaling Startups Your Way: Melissa's Real-Tech Talk
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40:42Join Sean and tech whiz, Melissa Kwan, as they unravel the allure and struggles of bootstrapping startups. Melissa dives into founding eWebinar and transforming pains into gains, all while crafting a business that perfectly suits her digital nomad lifestyle. She drops valuable gems on pricing pitfalls and the underrated power of slow growth. Don't …
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Navigating the Realities of Startup Life with E-Man and Ky
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1:14:32Send us a text Embark on a thrilling journey with E-Man and Ky, the dynamic duo behind Through Him, as they spill the beans on diving into the business world. Think of it like hitting the gym – it's not about quick wins but building lasting strength and skills. We're here to guide you through the ups and downs of entrepreneurship, from setting up w…
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Charting a Legacy: Navigating the Waters of Financial Literacy and Asset Protection with Scherrie
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1:03:29Send us a text Picture your life's work, your legacy, slipping through your fingers because of a simple oversight. This nightmare scenario is what Shreve, a seasoned lawyer with a poignant family narrative, and I tackle in our latest podcast episode. We're dedicated to steering you away from the treacherous shoals of financial illiteracy and inadeq…
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Are you a manager dreading the difficult task of firing someone? Learn how to handle this challenging situation with professionalism and efficiency in this episode of Bootstrappers. Gwenn and Jeremy share their expertise on the best ways to handle one of the most difficult aspects of being a boss - firing someone. We'll guide you through the proces…
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Three Questions to Increase Your Leadership Game
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21:30Are you a leader looking to enhance your skills and make a difference? Look no further! In this episode, Gwenn shares the three crucial questions that every leader should ask themselves to up their leadership game. Join us as we dive into these thought-provoking questions and gain valuable insights into effective leadership. Don't miss out on this …
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Crafting the Ultimate Business Persona with James L. Bond
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1:04:53Send us a text Have you ever wondered what it's like to go from a technical expert to a sales sensation? Meet James L. Bond, the behavioral management guru and advertising maestro who joins us to unravel his transformative journey. He turns the sales game on its head, showing us that with the right mix of passion and a consultative approach, even t…
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Mowing Down Barriers to Build a $30 Million Tech Empire with Bryan Clayton
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1:04:55Send us a text Ever wondered how a teenager's lawn mowing side hustle could blossom into a multimillion-dollar landscape empire? Brian's extraordinary journey from pushing a lawn mower to piloting a tech startup unveils the untapped potential within the entrepreneurial spirit. Today, he sits down with us to map out his path to building a $10 millio…
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Are you tired of searching for the elusive secret to earning $1 million a year with your business? Learn the three key strategies that have helped less than 4% of businesses achieve this success. Jeremy Aspen shares his expertise and personal experience on how to make a million dollars a year. Don't miss out on this valuable information and learn h…
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Fusing Grit and Grace: Barbie the Welder's Journey Through Metal and Mindsets
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1:16:34Send us a text When Barbie the Welder first struck an arc, she didn't just fuse metal; she sparked a revolution in the trades. Join us as we sit down with the powerhouse sculptor, author, and social media influencer who's cutting through steel and stereotypes alike. Our candid chat traverses her personal saga of resilience, from facing down naysaye…
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From Side Hustle to Tech Stardom: The PickFu Story
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29:36Dive into the journey of John Li, PickFu's co-founder, as he switches from tech giant to startup maven, revealing how keen insights and customer feedback fuel software success. Discover how PickFu's savvy use of AI revolutionizes consumer research, making it a game-changer for all seeking market savviness. Here are a few of the topics we’ll discuss…
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The Grind, a Great Tool For Underdogs But at What Cost?
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1:00:23Send us a text Ever feel like the underdog in a world where the odds are stacked against you? That's the spirit Squalle and I embody as we reminisce about our journey from gritty training partners to trailblazers in the fitness industry. Our conversation isn't just about the hustle—it's a raw, unfiltered look at the sacrifices made and the personal…
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Struggling to stay organized while juggling work and family life? Learn how you can stay organized at work without having to sacrifice the other important parts of your life. In this episode of Bootstrappers, Gwenn is joined by Lindsey Savage, an impressive working mom who has mastered productivity. Lindsey shares her three secrets to juggling fami…
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Do you want to start 2024 off with a bang? Join Gwenn as she shares her top tips on how to conduct a meaningful and practical year-end review. Learn how to rid yourself of bad habits, identify energy-sapping activities, set realistic goals, and enhance your time management and relationships. Her invaluable advice will help you take the plunge into …
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Joining Sean's SaaS Community: Free Access Offer
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5:57Summary Dive in with Sean as he spotlights the power of SaaS communities! Yearning for your feedback and eager to foster dynamic interactions, he unveils a thrilling offer for listeners to join his nascent community for free. Email or survey, choose your path to shape content that resonates with you. Hit play for an episode that bridges the gap bet…
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Marketing in an AI World: Risks & Opportunities
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6:45Summary Dive into AI's rapid evolution with Sean's latest panel experience! Uncover why businesses lag in tech adoption, the SEO balancing act, and making smart tech choices. Plus, learn to leverage AI for operational efficiency and potentially create market-worthy solutions of your own! Key Points Most businesses lack an AI strategy Keep pace with…
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SaaS Strategies in a Crunch: Growth in Tough Times
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7:34Summary Dive into the seismic shifts challenging SaaS companies in 2023's economic terrain! Sean unpacks the OpenView Benchmarks report, reveals key survival tactics for SaaS founders and CEOs, and uncovers the profitable edge AI integration offers. Tune in for insider insights to pivot, adapt, and outperform in a financial squeeze! Key Points SaaS…
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Stop Managing Passwords: The OTP Revolution
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6:46Summary Join Sean as he decrypts the world of design patterns, focusing on the seamless authentication revolution of one-time passcodes (OTPs). Learn why rehashing old methods is out, and how adopting OTPs can be a game-changer for software innovation and security. Key Points Design patterns simplify innovation. OTPs transform authentication. Passw…
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Summary Dive into the SaaS world with Sean as he unpacks OpenView's latest report. Discover why growth rates are plummeting and which outliers are defying the trend. Is it all about AI and vertical specialization? Tune in for insights on the evolving SaaS landscape amidst a shifting economic climate. Key Points SaaS growth rates decline sharply Eco…
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Future Tech Fails: Learn From Design Oversights
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6:27Summary Ever excited about creating something groundbreaking only to overlook essentials? Sean dives into the innovation paradox, sharing epic blunders from tech history and tips to ensure new solutions don't leave users cold, or in some cases, literally cold. Tune in and learn to innovate without sacrificing the crucial bits! Key Points Understand…
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Five Ways Virtual Assistants Fix Toxic Company Culture
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19:21Are you looking for ways to prevent a toxic work environment in your business? Look no further! Join Gwenn and Jeremy on this episode of Bootstrappers as they share the five ways virtual assistants can help fix toxic company cultures. Gain valuable insights on how to foster a highly productive and positive work environment, especially when working …
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