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Embrace New Challenges by Finding Joy in the Learning Curve


In this episode of Establishing Your Empire, host Daran Herrman interviews guest Mike Trigg, an experienced Silicon Valley executive, entrepreneur, and author with an impressive career spanning over 25 years. Trigg discusses how he followed his interests throughout his various career transitions and found joy in climbing the learning curve of new challenges. He emphasizes the importance of enjoying your job and being passionate about what you do, as well as not being intimidated by entering new industries and embracing the possibilities that come with naivety. Trigg also shares insights on entrepreneurship and discusses his recently published novel, Bit Flip, which offers readers an authentic insider’s view of the corrupting influences in technology startups. Listeners will gain valuable insights from Trigg’s experiences and career journey in the tech industry.

Listen on: Apple Podcasts | Spotify | YouTube | Pandora

“Stick with your vision and keep working on stuff… someone else is going to do it if you don’t… Use your imagination more and more. It’s not just about being an entrepreneur, it’s about being a gritty, dynamic person that survives chaos.”

Key Topics Discussed:

  1. Business and Money: The conversation begins with a discussion about the influence and challenges of money in business settings. It emphasizes the need to be aware of financial dynamics and their impact on business objectives and problems.
  2. Strategic Partnerships and Community Building: The speakers delve into the concept of creating an “information pack” in business, focusing on the importance of strategic partnerships, community engagement, and the role of investors and advisors in scaling a business.
  3. Business Goals and Revenue Generation: The dialogue touches upon the balance between focusing on future goals and the necessity of revenue generation in business ventures. The importance of having clear, achievable goals is highlighted.
  4. Team Dynamics in Startups: The discussion shifts to the significance of assembling the right team or “pack” in startups, stressing the need for diverse skills, clear communication, and aligned expectations among team members.
  5. Educational Transformation through Technology: There is a significant focus on the transformation of education through AI and blockchain, discussing personalized learning experiences and the potential for these technologies to revolutionize the educational landscape.
  6. Personal Entrepreneurial Journeys: The speakers share their personal backgrounds and experiences, providing various perspectives on entrepreneurial journeys and the lessons learned along the way.
  7. Equity and Startup Partnerships: The conversation explores the complex topic of equity distribution in startups, addressing the challenges of aligning contributions and expectations in partnerships.
  8. Blockchain Technology Potential: The potential applications of blockchain technology are discussed, particularly in education, emphasizing the need for innovative applications beyond its current usage.
  9. Writing and Publishing a Book: Michael Devellano shares insights into his process of writing and publishing a book, including challenges, strategies, and the importance of marketing and promotion.
  10. Advice to Younger Individuals and Entrepreneurs: The speakers provide personal advice for younger individuals and budding entrepreneurs, focusing on perseverance, vision, risk-taking, and the importance of learning from failures.
  11. Future Plans and Aspirations: Devellano talks about his future plans, particularly in the fields of AI and education, with a strong desire to provide mass-customized education and contribute positively to these sectors.
  12. Reflections on Personal Motivations and Legacy: The episode concludes with reflections on personal motivations for writing and contributing ideas, along with thoughts on the legacy and impact one hopes to leave, especially in entrepreneurial and technological spaces.

Devellano’s perspectives provide a blend of practical advice, personal anecdotes, and forward-looking ideas, particularly around technology and education. The conversation is engaging, informative, and offers valuable takeaways for anyone interested in entrepreneurship, technology, and personal growth.

Bit Flip: A Novel
About Mike Trigg

Mike Trigg shares his journey from working in politics as a press secretary on Capitol Hill to the tech industry during the .com boom. He talks about his experience as a product manager at Threecom and how that role gave him a solid foundation in business and technology. He then dives into his time at Octane Software and Epiphany, which paved the way for many of his subsequent career moves.

In the first few minutes Trigg also discusses the importance of product management roles, such as project management, product management, and product marketing. These roles involve coordinating logistics, straddling the business and technical sides, and advocating for products once they are built. He emphasizes how crucial these skills are for any entrepreneur, as they involve getting people with different skills and expertise to work together towards a common goal.

[00:16:00] Mike Trigg emphasizes the significance of having the right technology and a strong go-to-market strategy for product success, using examples of some of the biggest smash hits of the past 20-30 years.

[00:19:00] Mike Trigg talks about High 5’s success in various regions, its eventual decline, and the lessons he learned from his time in the social networking space.

[00:21:00] Mike Trigg shares advice on career pivots and transitions, emphasizing the importance of following your interests and climbing learning curves.

[00:23:00] Daran Herrman and Mike Trigg discuss the art of knowing when it’s time to move on in your career and how to make that transition smoother.

[00:24:00] Mike Trigg shares insights on having open and honest conversations with yourself and others about career dissatisfaction, and the importance of finding support through various sources.

[00:42:00] Mike Trigg explains his motivation for writing a novel instead of a memoir about his experiences in the tech industry, highlighting the lack of authentic fiction literature about the tech sector.

[00:44:00] Mike discusses the evolution of the tech industry, touching on its initial promise of improving lives and how the perception has shifted with the rise of “big tech” companies.

[00:45:00] Mike Trigg delves into the main theme of his book, ambition, and how it explores the moral dilemma faced by a startup executive who discovers potential fraud within the company.

[00:47:00] Mike explains how the prevalent structure of venture-backed Silicon Valley startups can enable and encourage unethical behavior due to the lack of independent fiduciary oversight and transparency.

[00:49:00] Comparing the .com boom to the current tech industry, Mike highlights the difference in liquidity events for venture investors and the implications of companies staying private for longer periods.

00:58:00 – Mike Trigg discusses pursuing your passions and enjoying the process, not just the outcome. He shares his experiences with successes and failures in the tech industry and how the desire for achievement can overshadow enjoyment of the job.

01:00:00 – Mike talks about the importance of being emotionally and financially sustainable as an entrepreneur. He shares his personal experience with a gaming startup and how it affected him both financially and emotionally.

01:01:00 – Daran Herrman emphasizes the importance of having multiple pillars in life and not just focusing on one thing. They discuss the challenges of maintaining balance and insulation in life.

01:02:00 – Mike shares how he bounced back from the gaming startup failure by relying on strong relationships in both personal and professional life. He highlights the importance of maintaining and nurturing those connections.

01:03:00 – Mike talks about the value of the golden rule in the tech industry and how nurturing relationships can lead to new opportunities.

01:04:00 – Daran asks Mike how he would like to be remembered. Mike shares that he now focuses more on relationships, family, and personal satisfaction rather than achievements and legacy.

01:05:00 – Mike discusses the challenge of focusing on personal satisfaction in an environment like Silicon Valley, where external measurements of success are prevalent. He emphasizes the importance of supporting oneself financially while also not worrying too much about legacy.

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