How th Unf**k Your Startup

How th Unf**k Your Startup

By Dan HurwitzBusinessEntrepreneurship
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How th Unf**k Your Startup episodes

  • The Fine Line Between Passion and Strategy in Startup Leadership

    Jeff Hirsch is the Founder & CEO of Executive Guru and a leader with decades of experience in tech, media, and advertising. He’s led multiple businesses to successful exits, and now he advises startups on growth strategies, leadership, and navigating the challenges of scaling.

    In this episode, Jeff talks about what it takes to lead a startup effectively—balancing the emotional investment founders have in their businesses with the practical decisions needed to grow. We broke down everything from building leadership teams that can scale with the company, to making tough calls when you don’t have all the data, and getting the most out of your board.
    If you're struggling to balance your passion with the demands of growing a company, Jeff has practical ideas to help you find that sweet spot.

    41 min
  • Relentless Resilience: Exploring Joe De Sena’s Approach to Entrepreneurship

    Joe De Sena joined me this week to share his journey from selling fireworks as a kid to building Spartan, a global obstacle course race company known for its intense races, ranging from 5K sprints to ultra-endurance events.

    Throughout Spartan’s expansion across 40+ countries, Joe remains focused on his mission to help people transform by pushing beyond their physical and mental limits.
    On the podcast, Joe shares what it takes to keep going when things get tough, how he leads a team of 500 with a purpose-driven focus, and why starting a business is like running one of Spartan’s Death Races.
    We also discuss how Spartan stays true to its mission, how Joe evaluates business risks, and the value of having the right team around you.

    38 min
  • B2B Sales Are Changing - Here’s How Founders & CROs Can Adapt

    Warren Zenna is founder of The CRO Collective, and has over 25 years of experience in B2B sales and marketing. He’s made it his mission to redefine the role of CROs and help companies navigate the complexities of revenue generation.

    Founders face a rapidly changing market that demands adaptability, self-awareness, and a willingness to challenge conventional wisdom. Warren shared a lot of advice for how founders and CROs can make more informed decisions about their growth strategies - from rethinking traditional sales approaches to balancing short-term gains with long-term vision.
    That’s what this blog will focus on - but the whole episode covers that and much more.

    54 min
  • Can AI Help us Become More Human? With Ioanna Mantzouridou Onasi, Co-Founder and CEO of Dextego

    Ioanna Mantzouridou Onasi is an applied AI thought leader with a mission is to help people and organizations thrive by developing soft skills like communication, empathy, and leadership. Through Dextego, she’s showing how AI goes beyond automation to drive human potential. With a background that spans founding a sustainable fashion company at 16 to leading talent development at a B2B SaaS AI startup, Ioanna’s experience is as diverse as it is impressive.

    This conversation digs into how AI can free us up to focus on human connections and creativity. Ioanna breaks down the practical ways AI can enhance, rather than replace, our ability to lead, collaborate, and problem-solve.

    If you're looking for ways to leverage AI in your startup

    40 min
  • How to Scale Yourself While Scaling Your Business, with Matthew Yahes, CEO of Extend Your Team

    Matthew Yahes has been around the block a few times when it comes to building businesses. As the CEO of Extend Your Team, he's taking the lessons he's learned from either starting, buying, or growing four different companies and putting them to work to help others scale up.

    These days, Matthew is connecting businesses with top-notch talent in the Philippines, showing founders how to build strong teams without breaking the bank. Whether it's e-commerce, restaurants, or staffing, Matthew's seen it all - and he's sharing the good, the bad, and the ugly of his story.
    In this episode, we went particularly deep into the evolution of a founder's role, from hands-on operator to strategic leader. We explore the stages of a founder's journey, the importance of hands-on experience, strategic time management, and the art of delegation.
    Matthew has a gold mine of tips on how founders can effectively grow with their companies. So whether you're just starting out or looking to scale your existing business, this conversation is packed with practical advice.

    51 min
  • Why Your Go-To-Market Strategy Is Failing And The Critical Insights to Transform Your Startup's Growth, with Janine O’Neill, Co-Founder of ElevenX Talent

    Janine O'Neill, co-founder of ElevenX Talent, has more than 20 years of experience helping startups find and hire top executive talent. With an MBA from UC Berkeley and certification as an Integral Coach, Janine leverages her background in recruiting, leadership development, and advising to partner with early-stage and growth-stage companies to build out their go-to-market teams.

    In this episode, Janine shares her learnings on navigating the challenges of hiring the right executives at the right time. She breaks down the evolving dynamics between sales, marketing, and customer success, and reveals the red flags that make candidates wary of joining certain startups.
    Janine's wisdom and tactical advice are a must-listen for any founder looking to avoid costly missteps and put their startup on the track to success. Her unique perspective, honed through years of working with top-tier startups and VCs, is both eye-opening and immediately actionable.
    Here are some of the key topics from our conversation:
    [02:30] Hiring the right go-to-market executives at the right time
    [27:51] Building trust in go-to-market hires' expertise
    [29:29] Setting realistic expectations for ramp-up time
    [36:11] Recognizing when a product is not ready for the enterprise market
    [41:24] The importance of grit and self-awareness in founders

    46 min
  • Why Your Company is Falling Behind on AI and the Critical Ways to Integrate It with Ryan Staley, Founder and CEO of Whale Boss

    Ryan Staley, CEO of Whale Boss, is a seasoned revenue generation expert who has consistently built highly successful revenue machines from the ground up, leading to multiple profitable exits. His impressive track record includes 18 President's Club awards and generating over $150M in revenue. Having mentored more than 800 revenue leaders, Ryan offers unique insights on navigating common pitfalls and driving efficient growth across various industries.

    This week, Ryan delves into his recent journey of leveraging AI to help companies unlock new possibilities and stay ahead of the curve in an increasingly competitive landscape. He shares his firsthand experience with the AI transformation process and offers a comprehensive overview of the current AI landscape, discussing both the opportunities and challenges that companies may face when integrating AI into their operations. Additionally, Ryan provides a practical "starter kit" specifically tailored for B2B tech startups looking to effectively integrate AI into their sales and marketing processes, enabling them to optimize their efforts and achieve better results.
    Here's a breakdown of the highlights:
    [03:56] From sales leader to AI growth expert
    [08:14] Investing in post-sale customer relationships
    [11:14] 3 lessons for sales executives and leaders
    [16:31] Misaligned expectations in sales leadership roles
    [23:54] Perspective on the AI transformation landscape
    [29:14] Obstacles in adopting AI effectively
    [32:13] B2B tech startup AI starter kit
    [36:22] Connecting with Ryan for AI advice

    38 min
  • Joe Gravino’s Proven Strategies for Hiring Revenue Leaders for PE-Backed Companies

    Joe Gravino, VP of GTM Search at Falcon, brings expert insight into hiring the right revenue leaders for private equity-backed companies. With a mission to build better teams that drive returns, Joe and his team at Falcon have helped 250+ portfolio companies and 50+ PE firms find the best-fit CROs, CFOs, and VPs of Sales.

    In this episode, Joe shares his knowledge on avoiding costly mis-hires. He breaks down the most important traits to look for, the right questions to ask, and the pitfalls to avoid when bringing on a new CRO or VP of Sales. His practical advice is a must-listen for any founder or investor looking to nail their next crucial revenue hire.
    Here's what Joe and Dan discuss in this episode:
    [02:13] Joe's journey from new grad to leading Falcon's GTM executive search practice
    [12:11] The dangers of hiring a "strategic" CRO too early
    [18:48] Assessing a CRO candidate's track record, skill set, and ability to execute
    [28:00] Balancing industry expertise vs. raw leadership talent
    [30:28] How unrealistic expectations can sabotage a search
    [33:49] Interview red flags that scare off top candidates
    [42:29] The importance of full transparency about challenges that need to be solved

    45 min
  • Escaping the Venture Capital Trap: Growing Your Startup on Your Own Terms with Andrew Dumont, Founder and CEO at Curious

    In the latest episode of *How to Unf**k Your Startup*, I sat down with Andrew Dumont, a startup veteran whose entrepreneurial journey began at the tender age of 18 when he co-founded Tatango, a group text messaging startup that raised an angel round and set the stage for his future endeavors. Since then, he has been a driving force behind numerous successful startups, wearing many hats along the way.

    From his time as a key player at betaworks, a startup studio that has invested in household names like Tumblr, Medium, and Kickstarter, to his role as CMO at Bitly, where he built and led the revenue and go-to-market teams, Andrew has demonstrated a knack for building and scaling companies. Recently, he served as the CEO of Stamped, a SaaS company in the e-commerce space, and also led multiple brands under the umbrella of Tiny, a publicly-traded holding company. Now, as the founder and CEO of Curious, an investment firm and holding company, Andrew is on a mission to help other entrepreneurs navigate building their startups.

    Andrew shared his unique perspective on the venture capital landscape, exploring the hidden pitfalls that can accompany venture funding, the importance of aligning founder and investor incentives, and the mental and emotional toll that the constant pressure to scale rapidly can take on both founders and their teams. But perhaps most importantly, our conversation also shed light on the often-overlooked alternatives to the traditional venture capital path. From bootstrapping to revenue-based financing, we delved into the strategies and approaches that can help founders maintain control over their vision, build resilient and profitable businesses, and ultimately achieve their goals on their own terms.

    Whether you're a first-time founder just starting out or a seasoned entrepreneur looking to get in the game once again, this episode will give you a lot to chew on.


    Here are the four points that stuck with me after our conversation:

    - The Pitfalls of Misaligned Incentives (09:26)

    - The Fatigue of Constant Pivots (09:58)

    - Bootstrapping for Autonomy and Success (34:10)

    - Exploring Alternative Financing Options After Bootstrapping (35:08)

    42 min
  • Frank Casale Reveals Critical Components Every AI Startup Needs to Succeed in a Saturated Market

    Frank Casale, founder of the Institute for Robotic Process Automation & Artificial Intelligence, joined the latest episode of How To Unf**k Your Startup to discuss the future of AI and the evolving landscape of startups. With more than 25 years of experience in emerging tech, Frank brought a lot of knowledge and valuable perspective to the table.

    Throughout this conversation, Frank shares his insights on navigating the complex world of AI and startups. From identifying common pitfalls and misconceptions to exploring the potential for new startup models, he offers a well-rounded look at the state of the industry and where it's headed.
    Here's a breakdown of the key topics we covered:
    - [03:20] Frank's journey from outsourcing to RPA and AI
    - [05:52] The self-inflicted wounds of startup founders
    - [08:36] The three camps of AI perception
    - [13:56] AI startups: Pitfalls and potential
    - [17:27] The future of AI and the startup landscape
    - [22:33] Bringing AI into your organization
    - [24:42] The call center of the future
    - [26:58] Surviving in a world of tech giants

    48 min

About How th Unf**k Your Startup

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"How To Unf**k Your Startup" is an audacious, groundbreaking podcast series that targets the heart of tech entrepreneurship, focusing on Series A and Series B startup founders desperate for strategies…