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.

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.

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.

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

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.

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

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

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

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)

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

On the latest episode of How to Unf**k Your Startup, I had the pleasure of sitting down with Zan Bennett, Principal at Exactius Capital Management. With a wealth of experience in growth marketing and leadership, Zan has collaborated with world-class executives, strategic capital, and global teams to accelerate growth-stage companies into hypergrowth. His expertise spans a diverse range of sectors, including Consumer, E-commerce, two-sided marketplaces, and B2SMB SaaS. Prior to his role at Exactius, Zan owned and ran a company focused on scaling social impact ventures, which built lasting businesses from scratch across industries such as healthcare, climate, consumer, high-end design, and SaaS. Throughout our conversation, Zan shared invaluable insights on navigating the complex landscape of venture-backed startups, offering lessons for both investors and founders. We explored the intricate dynamics and interdependencies within the startup ecosystem, emphasizing the importance of building authentic relationships, adapting to evolving market conditions, and maintaining a customer-centric approach.

Zan's unique perspective, having worked closely with investors and founders, shed light on the shared goals and challenges these players face. From the investor side, he discussed the art of seeing beyond polished pitches to identify true potential and the need for caution when evaluating startups amidst industry hype cycles. For founders, Zan stressed the criticality of staying connected with customers throughout the startup journey and aligning the entire team around focused objectives. These insights, among others, provide a roadmap for successfully navigating the startup ecosystem and driving sustainable growth. If you're an investor looking to make smarter decisions or a founder striving to build a thriving company, this episode is packed with actionable advice you won't want to miss.

This week on How to Unf**k Your Startup, we welcomed Alex Kottoor, a seasoned entrepreneur and business leader with over two decades of experience driving profitable growth in startups, SMBs, and Fortune 500 companies. Alex started his career at CDW, where he honed his skills in solving customer problems through technology. He then co-founded his first SaaS company, SceneDoc, which he successfully grew and exited. Now, as the founder and CEO of Dena Growth, Alex is turning his attention towards helping early-stage founders navigate the challenges of scaling, particularly around go-to-market strategy and sales. Having been a founder himself, Alex knows firsthand the challenges they face when transitioning from founder-led sales to a dedicated sales team. In the early stages of a startup, founders often wear multiple hats, including that of the head salesperson. While this hands-on approach is necessary to understand customers and craft a winning sales formula, there comes a point where founder-led sales can become a bottleneck to growth. Knowing when and how to make the transition to a dedicated sales team is a critical inflection point that can make or break a startup's trajectory. In this episode, Alex shares his framework for navigating this transition strategically, from laying the groundwork with deep customer immersion to codifying a repeatable sales playbook to making the right first sales hires. Founders will come away with a clear roadmap for scaling sales beyond themselves while avoiding common pitfalls that can derail momentum.

This episode of How to Unf**k Your Startup features a chat with Dorothy Chang, Co-Founder at Lynx Collective, an amazing community for tech startup founders and aspiring entrepreneurs. Dorothy's been a rising star in the NYC tech scene for over two decades, killing it in roles in PR, marketing, venture capital, and nonprofit leadership. Make no mistake, she knows her stuff. Throughout the conversation, Dorothy broke down why crafting an unforgettable story is non-negotiable for every early-stage startup. She dug deep into what separates a dull story from a holy-s***-I-need-to-tell-everyone-about-this story, how to sidestep the awkward rookie blunders that'll make people's eyes roll, and why even the most naturally gifted storytellers need to put in the reps to keep their skills sharp.

In the latest episode of How to Unf**k Your Startup, I had the opportunity to sit down with David Weiss, Chief Revenue Officer at The Sales Collective.

David is an expert when it comes to developing value propositions that genuinely resonate with customers. He has a background in data-driven sales strategies and a proven track record of building sustainable growth. During our conversation, we dove deep into the craft of streamlining your messaging and focusing on the outcomes that matter most to your target audience.

Throughout the episode, David provides practical frameworks and real-life examples that can help any startup crystallize its product's value and drive meaningful results. I highly recommend setting aside some time to listen to our conversation. Trust me, David's insights can help you navigate the challenges of startup life and set your company on the right path.

Michael Brenner is the Founder of Marketing Insider Group, a content marketing agency that helps companies reach, engage and convert new customers. With over 25 years of experience in sales and marketing, Michael has seen firsthand the challenges businesses face in capturing the attention of today's savvy, distracted buyers. As an author, keynote speaker and recognized leader in the content marketing space, he helps organizations rethink their approach to customer engagement.

In this episode of How to Unf** Your Startup*, Michael and I dove into the strategies startups must employ to reach buyers in an increasingly noisy marketplace. With loads of stories and hard-won insights, Michael shares his formula for crafting marketing messages that resonate and building an inbound engine that drives sustainable growth. Our conversation drives home the importance of a customer-centric mindset in all aspects of startup operations, from leadership to demand generation.