Podcast Summary:

The Big Impression – Michael Rubenstein on Founding Firsthand, AI, and the Future of Ad Tech
Episode date: October 15, 2025
Hosts: Damian Fowler (“A”) & Ilyse Liffreing (“B”)
Guest: Michael Rubenstein, Co-founder & CEO of Firsthand

Overview

This episode marks the launch of The Build, a new podcast series within The Big Impression, featuring in-depth, candid founder-to-founder conversations about what it really takes to build breakthrough technology businesses. Recorded at Advertising Week New York, hosts Damian Fowler and Ilyse Liffreing sit down with Michael Rubenstein—serial entrepreneur and former commercial leader at DoubleClick, AppNexus, and now co-founder of AI startup Firsthand. The discussion centers on navigating the transformational waves of tech innovation (from ad exchanges to AI), the shifting meaning of entrepreneurship, the future of brands in an AI-first world, and the perennial challenges of hiring, scaling, and finding the right co-founders.

Main Discussion & Key Insights

1. The Evolution from Intrapreneur to Entrepreneur

• Trajectory & Motivation

  • Michael shares his journey from early startup founder (while at university), to intrapreneur at giants like DoubleClick and AppNexus, to founding Firsthand.
  • Quote [01:57], Michael:

    “I view myself more as a builder and an innovator and a value creator more than an entrepreneur per se...the dynamism of business and innovation in business was where I wanted to spend my career.”

• Different Paths to Building

  • Highlighting that there’s no single path or template—companies can start with a monumental vision or by chipping away at niche problems that others overlook.
  • Quote [03:12], Mike O’Sullivan (host):

    “There's so many ways to build something...let's start with something really small and cumulatively build and see where it goes.”

2. Contrast: Intrapreneurship vs. Entrepreneurship

• Common Threads & Differences

  • Both require passion, problem-solving, and leveraging expertise, but entrepreneurship offers unrivaled agency and freedom.
  • Intrapreneurs must balance independence with maximizing the resources of larger institutions.
  • Quote [06:32], Michael:

    “With intrapreneurship, you...have to leverage the assets around you, or you’re not really capitalizing on the benefit of doing something inside a larger organization.”

• Agency & Scale

  • Even as a small startup, founders find themselves on equal footing in discussions with industry giants—founder-to-founder, CEO-to-CEO.
  • Quote [07:07], Mike:

    “You have unlimited agency...maybe we’ll build a whole new product based on this feedback. To me, that is one of the differences...this maximum agency.”

3. Innovation vs. Defense in Large Tech Companies

• The Thrill and Existential Importance of Growth

  • “Defending” a mature business is less engaging and often less successful than pursuing growth and innovation.
  • Quote [10:17], Michael:

    “Playing it safe will not keep you safe...it’s actually paradoxically the willingness to fail and take risks that will lead companies to succeed.”

• Canadian Wisdom & Full Push

  • Emphasis on the need for founders and innovators to play freely, embrace risk, and push limits (“full push” from F1 racing).
  • Quote [10:59], Mike:

    “You have to play at the red line of what you’re doing and that’s how these companies win.”

4. Building Teams & Hiring Philosophy

• Intentional Approach to Talent

  • Hiring high-potential, hungry, integrity-driven people, focusing on values and culture above specific prior experience.
  • Creation of internal development programs, like “AppNexus University,” and fostering a culture of constant learning and teaching.
  • Quote [12:37], Michael:

    "You hire people who are hungry...you create mechanisms like we did at AppNexus...and you think very intentionally about your company's values and culture as well."

• Carrying Lessons Forward to Firsthand

  • The same principles are being applied: prioritize passion and spongelike curiosity, especially in navigating a major tech shift like AI.
  • Quote [14:29], Michael:

    "We're looking for people who want to build the next platform and the next wave as well...bringing on people who are passionate about that, who are high potential, who want to be sponges and teach others..."

5. The AI Moment: Opportunity and Peril for Brands

• AI Parallels with Programmatic & Internet

  • Current AI wave is compared to early days of ad exchanges and the onset of online advertising: educational, evangelistic, but moving even faster now.
  • Quote [16:27], Michael:

    “This moment in AI reminds me a little bit more of those early days of the exchanges...This is an education and evangelism moment.”

• Existential Risks & The Fight for Brands

  • The risk: AI intermediating and diluting brands into commodities; the opportunity: brands mastering AI to build direct consumer relationships.
  • Firsthand’s mission: “Brand agent platform”—help brands use AI as their own interface, not lose control to tech giants.
  • Quote [18:28], Michael:

    "There's a scenario...where the consumer experience...is fully intermediated by these AI companies...brands become almost like brands on the Amazon marketplace, like totally interchangeable...I just think that's a bad outcome for the Internet, for consumers, and for brands."

6. Real-World Application: Brand Agents Example

• Explanation of Brand Agents

  • Instead of a static ad, brands send a dynamic, intelligent “agent” to engage and guide consumers throughout their journey—direct, personal, and contextual.
  • Quote [26:51], Michael:

    "You could think of brand agents as almost virtual brand representatives...instead of sending out an ad...you're sending out your brand agent to engage with a consumer..."

• Early Results

  • Brand agents have shown “bananas” results after a year-and-a-half of live use, fundamentally changing how brands interact with consumers.
  • Quote [28:28], Michael:

    "The results are bananas."

7. Co-Founder Selection & Complementary Vision

• Choosing Co-Founders

  • Friendship, long-shared history, vision around AI as a new communication medium, and complementary skillsets drove the founding team.
  • Quote [22:16], Michael:

    “What I look for generally in co-founders, I think shared values is really important. Shared vision...and complementarity...a one plus one equals three situation.”

• Seeing Around Corners

  • Importance of having partners who can anticipate industry shifts—John Heller’s background in Freewheel and vision for how ChatGPT changed the AI landscape.

8. Lessons on Scaling and Founding

• Founders’ Changing Role over Time

  • Founders must evolve from founding to executive leadership as the company grows.
  • Quote [30:49], Michael:

    "The job of a founder is to found a company. And once the company is founded, the founder doesn't really have a job anymore. The job...is to find a role on the executive team, and...do that job better than anyone else could..."

• Underestimating Talent Challenges

  • Hiring for early-stage startups is fundamentally different than for established companies; underestimated by many.
  • Quote [33:37], Mike:

    “I underestimated how hard it is to hire good people...People who are super successful...at a company of 200 or 100 [aren't always a fit] to be employee 4 or 5 or 6..."

• Thinking Big & Surrounding Yourself With Visionaries

  • It’s crucial to have ambitious mentors and team members who help challenge and expand your vision.
  • Quote [35:11], Michael:

    "Don't underestimate how significant your vision can be...It’s helpful to have great people around you..."

9. The Only Advice in 2025: Bet on AI

• AI Is the Future
  • All companies now must either be AI startups or AI transformation projects; those who leverage AI meaningfully will thrive.
  • Quote [36:53], Michael:

    “Every business today...is either an AI startup or an AI transformation. I am personally...all in on it...your business needs to be fundamentally about unlocking the value of AI and leveraging AI."

Notable Quotes & Memorable Moments

• [01:57] Michael Rubenstein: “I view myself more as a builder and an innovator and a value creator more than an entrepreneur per se.”
• [10:17] Michael Rubenstein: “Playing it safe will not keep you safe as a company. Playing it safe actually will cause you to fail.”
• [18:28] Michael Rubenstein: “There’s a scenario...where brands become almost like brands on the Amazon marketplace, like totally interchangeable...That’s a bad outcome for the Internet and for consumers and for brands.”
• [26:51] Michael Rubenstein: “You could think of brand agents as almost virtual brand representatives...engage with a consumer...guide the consumer through an entire consumer journey.”
• [35:11] Michael Rubenstein: “Don’t underestimate how significant your vision can be...you can accomplish so much more as an organization or as a team than as an individual.”
• [36:53] Michael Rubenstein: “Every business...is either an AI startup or an AI transformation...your business needs to be fundamentally about unlocking the value of AI and leveraging AI.”

Important Timestamps

• [01:57] Michael details his entrepreneurial path and mindset
• [06:32] On the balance of leveraging assets as an intrapreneur
• [10:17] Why ‘playing it safe’ is dangerous for companies today
• [12:37] Michael’s ‘learn and teach’ hiring philosophy at AppNexus and Firsthand
• [16:27] How the AI era mirrors and differs from the rise of programmatic
• [18:28] The existential fight for brands in an AI-mediated world
• [26:51] Example use case: how brand agents transform the consumer journey
• [30:49] The founder's ever-changing role as a company grows
• [36:53] The essential imperative for all businesses to embrace AI

Takeaways for Listeners

• There’s no single path to building impactful technology—success can come from small beginnings or big, world-changing visions.
• Intrapreneurship offers stability and resources, but “maximum agency” and freedom belong to entrepreneurs.
• The greatest risk for tech companies today is not innovating—“playing it safe will not keep you safe.”
• Company culture, values, and intentional talent development drive success, outlasting any single product or trend.
• The next era of digital marketing demands brands to leverage AI directly—risking commoditization if they cede control to intermediaries.
• Choosing co-founders and teammates is about shared vision and complementary strengths, not just resumes.
• Every business must now think of itself as "AI-native" or in transition—this is the foundational shift of the 2020s.

For First-Time Listeners

This episode is rich in practical wisdom, war stories, and real-time analysis of disruptive trends in ad tech and AI. Both for founders and brand leaders, the dialog between Michael and the hosts pulls no punches in addressing not just the "how" but the "why" of modern entrepreneurship.