David Hassell: CEO Chronicles - Navigating Crucial Decisions in the Scale-Up Journey

 

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Join David Hassell - CEO Chronicles: Navigating Crucial Decisions in the Scale-Up Journey ~ Funding, Strategic Pivots, and Staying True to Your Vision

Join the captivating conversation between renowned podcast host John Hittler and David Hassell, the visionary mind behind a thriving company 15Five, in the competitive landscape of HR solutions. In this exclusive episode on the 'Genius at Scale' podcast, David bares all about the rollercoaster ride of scaling up his business, from the brink of acquisition to becoming a market leader.

Journey to Resilience: Discover the untold story of how David faced the dilemma of potential acquisition, weighed the options, and ultimately decided to chart a bold path forward. Learn the invaluable lessons that shaped his leadership and defined his company's trajectory.

Unteachable Talents: Delve into the unteachable talents crucial for scaling success. From charisma to dogged determination, David shares insights into the intrinsic qualities that make a difference and elevate CEOs and entrepreneurs to new heights.

Strategic Pivots: Gain strategic wisdom as David unravels the critical decisions he made during the scaling process. From funding challenges to market positioning, explore the pivotal moments that defined his company's evolution.

CEO Chronicles: Get an inside look into the highs and lows of being a CEO. Navigate the complex landscape of annual planning, hear about successful methodologies, and discover the secrets behind fostering a unified, high-performing team.

Tune in now for a dose of inspiration, practical insights, and unfiltered truths from the heart of entrepreneurship. Don't miss this chance to tap into the genius at scale, as David shares his entrepreneurial journey with authenticity, vulnerability, and a wealth of wisdom. Subscribe and transform your scaling game today!


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David Hassell is a serial entrepreneur and presently Founder & CEO of 15Five, a SaaS company focused on helping managers and CEOs and get the insights from their people that they need to be highly effective, and to build great teams and organizations. He formerly served as President of the San Francisco chapter of Entrepreneurs'​ Organization, and was named "The Most Connected Man You Don't Know in Silicon Valley"​ by Forbes, who has also featured him as an expert on entrepreneurship. In 2004, he co-founded Kite Adventures, an adventure travel company offering guided downwind tours and pro-coached kiteboarding camps in northeast Brazil. 

Prior to that, in 1999 he co-founded Endai Worldwide, a NYC-based Internet marketing and services firm, and served as the company's CTO through 2006.  Endai has been recognized on the Inc 5000 list of fastest growing private companies in America.

CEO 15Five

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Here’s a glance at this episode…

Join the captivating conversation between renowned podcast host John Hittler and David Hassell, the visionary mind behind a thriving company in the competitive landscape of HR solutions. In this exclusive episode on the 'Genius at Scale' podcast, David bares all about the rollercoaster ride of scaling up his business, from the brink of acquisition to becoming a market leader.

  • 18:20 - Critical Decision During Series A Funding 

    • David Hassell faced a pivotal moment during the Series A funding where investors expressed second thoughts.

    • Despite the tempting offer of a significant financial gain and the possibility of not having to work again, Hassell chose to sign the term sheet and continue building the company.

    • This decision was driven by a desire to see the impact the company could have and a determination to pursue the mission.

  • 20:55 - Unteachable Talents for Scaling 

    • The discussion revolved around unteachable talents crucial for scaling a company.

    • Charisma was highlighted as an example of an unteachable talent, emphasizing its importance in recruiting, fundraising, talent attraction, and sales.

    • David also mentioned the determination and relentless pursuit of goals as another unteachable talent he values personally.

  • 26:35 - Annual Planning Process 

    • The annual planning process involves an iterative approach within the executive team.

    • It begins with defining the company's vision and goals, then involves individual leaders gathering input from their teams.

    • The process includes identifying cross-functional dependencies to avoid silos and ensure a unified company-wide vision.

    • Board approval is sought, and the finalized plan is rolled out to the entire company.

  • 31:17 - Biggest Mistake and Learning from Competition 

    • David shared a significant mistake where the company lost its market leadership to a competitor.

    • The mistake was not being singularly focused on the ideal customer initially, leading to a lack of alignment and momentum.

    • The key lesson was the importance of being laser-focused on one customer profile to avoid spreading marketing too thin and maintaining product focus.

  • 38:09 - Information Consumption and Opting Out of Noise 

    • David discussed his approach to information consumption, inspired by Tim Ferriss' idea of a news fast.

    • He emphasized the significance of less frequent but high-quality information intake, believing that important stories will find their way.

    • David participates in selected networks, checks Twitter occasionally, and engages in specific groups for tech and SaaS leaders.

    • To gain diverse perspectives, he reads news from various political lenses without identifying with any specific ideology.

Tune in now for a dose of inspiration, practical insights, and unfiltered truths from the heart of entrepreneurship. Don't miss this chance to tap into the genius at scale, as David shares his entrepreneurial journey with authenticity, vulnerability, and a wealth of wisdom. Subscribe and transform your scaling game today!

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David Duccini - Flounders, Founders, and the Art of Risk

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Erik Malin: From Dot-Com Dreams to Scaling Realities