In this episode of The Khanversation with Imran Khan, Imranspeaks with Adam Singolda, founder and CEO of Taboola. From coding in Israel’s elite cyber unit to raising funds at a bat mitzvah, Adam recounts his unique path to building one of the largest adtech companies on the open web. He sharesthe highs and lows of Taboola’s early days, the pivotal moments that defined the company, and how he introduced a guaranteed revenue model that transformed publisher relationships. The conversation also explores Taboola’s publicjourney, recent product expansion into performance advertising, and Adam’s take on the future of the adtech industry.

In this episode of The Khanversation with Imran Khan, Imransits down with Michael Strain, professor at Georgetown University and senior fellow at the American Enterprise Institute, for a deep conversation on U.S. trade policy. Together, they explore the implications of tariffs, how global manufacturing and employment trends have evolved, and why common narratives around outsourcing and trade deficits may miss the mark. Michael challenges widely held beliefs on American manufacturing decline, discusses the politicalversus economic weight of trade debates, and offers perspective on strategic reshoring of critical industries. The two also probe market reactions, including bond yields and currency movements, and the potential fallout of ongoing trade tensions.

In this episode of The Khanversation with Imran Khan, Imran sits down with Somesh Dash,General Partner at IVP, to reflect on two decades of venture capital experience. Somesh shares his early days in the industry, IVP's growth, and the traits of enduring founders. They explore venture trends, including IPO timing, the rise of SPVs, and the impact of AI. Imran and Somesh dive into lessons from Snap, Discord, and Rubrik, while examining the balance between investor influence, founder evolution, and long-term company building. An honest, thoughtful take on tech investing from two long-time friends and insiders.

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[00:00:00] Introduction and early friendship between Imran and Somesh.

[00:01:25] Somesh’s experience investing in Snap and working with Evan Spiegel.

[00:06:04] What makes a great founder: evolution, grit, and leadership.

[00:10:04] The importance of optimism and instinct in building companies like Discord.

[00:14:12] Somesh’s origin story: growing up in Silicon Valley and discovering venture capital.

[00:18:56] Why Somesh stayed at IVP for over 20 years and how the firm has evolved.

[00:23:04] How globalization and distributed workforces have changed venture.

[00:28:04] Why more companies are delaying IPOs and Somesh’s take on going public.

[00:36:15] Reflecting on Snap’s IPO journey and its long-term impact.

[00:39:14] The downside of too much capital and the rise of SPVs in venture.

[00:43:21] Scout programs in venture: benefits, risks, and IVP’s approach.

[00:49:28] The AI wave: Somesh’s view on where it's going and how IVP is participating.

Links:

Imran Khan on X: https://x.com/dottkhan

Imran Khan on LinkedIn: https://www.linkedin.com/in/dotkhan

Somesh Dash on LinkedIn: https://www.linkedin.com/in/someshdash

IVP: https://www.ivp.com/

In this episode of The Khanversation with Imran Khan, Imran speaks with Andrew Dudum, founder and CEO of Hims & Hers Health. Andrew shares the journey from his early entrepreneurial days—dropping out of Wharton and co-founding Atomic—to launching one of the fastest-growing digital health companies. He explains how a regulatory shift opened the doors to virtual care, the tech stack powering scalable patient outcomes, and how Hims & Hers is redefining access and quality across healthcare. Andrew also digs into the company's bold vision, how AI will reshape the patient experience, and why he’s building for a 20-year horizon

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(00:00:00) Andrew's early background and journey to entrepreneurship

(00:01:34) Identifying the consumer healthcare gap and launching Hims & Hers

(00:03:08) Dropping out of Wharton and shifting from music to business

(00:06:03) Early career at Talkbox and lessons from its acquisition

(00:08:54) Learning the importance of focus and conviction

(00:10:42) Regulatory trigger that sparked the digital health opportunity

(00:13:05) Naming Hims & Hers and building a brand around inclusivity

(00:14:28) Raising early capital and articulating the long-term vision

(00:16:00) Using data and tech to improve patient outcomes

(00:20:20) Delivering personalized care through technology and scale

(00:22:06) What drives Hims & Hers' rapid growth

(00:25:09) Strategy for scaling from 2 to 10+ million members

[00:28:06] Deciding which care categories to launch next

(00:30:53) International expansion plans and timing

(00:33:14) Weight loss market strategy and debunking GLP-1 hype

(00:36:47) Comparing the platform to Netflix for healthcare

(00:38:06) Generic medications and structural problems in access

(00:39:49) Thoughts on competition and market dynamics

(00:42:36) How AI will transform diagnostics and provider tools

(00:45:33) Operating as a fully remote company and hiring strategy

(00:49:15) Talent scaling and performance management philosophy

(00:51:48) What’s misunderstood about Hims & Hers and Andrew’s long-term vision

Links:

Imran Khan on X: https://x.com/dottkhan

Imran Khan on LinkedIn: https://www.linkedin.com/in/dotkhan

Andrew Dudum on LinkedIn: https://www.linkedin.com/in/andrewdudum

Hims & Hers: https://www.hims.com/

Imran’s illustrious career as a Wall Street heavy hitter, C-Suite tech operator, and hedge fund founder has been powered by a quest to learn. With the help of his guests, Imran will dive deep into areas outside his own expertise to have Khanversations that spark curiosity and inspire learning.