Startups grow faster and avoid costly mistakes when they learn from those who came before them. In each episode, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member. Tap follow and enable notifications to stay ahead of the game.
Yotam Segev is the co-founder and CEO of Cyera, one of the fastest-growing cybersecurity startups in the world. In this episode, he joins Logan to talk about scaling Cyera from 100 to 550 employees in under two years, what it takes to operate at that speed, and why going slow can actually be riskier. They cover lessons from a tough go-to-market year, the emotional conviction behind choosing data security, and h...
Blake Scholl, founder and CEO of Boom Supersonic, is leading the boldest effort in decades to bring back commercial supersonic flight—this time with product-market fit.
We talk about what went wrong with the world’s first try at supersonic commercial aircraft (launched in the 70s), why Boeing hasn’t introduced a new plane in over a decade, and how Blake’s startup is building a jet that flies...
College sports are going through massive changes—from athlete pay drama to superconference realignment and transfer portal chaos, not to mention the giant class action lawsuit playing out now.
Matt Brown, the publisher behind Extra Points and one of the top experts on the business of college athletics, joined the show to break it all down. We walked through the full history of college sports...
In this episode, Derek Thompson (Writer, The Atlantic) delves into the tumultuous nature of Trump’s trade policies, especially regarding tariffs, and how they impact American manufacturing and global markets. They discuss the constant changes in policy, the resulting uncertainty for industries like automotive and aerospace, and the mismatch between Trump’s ‘madman strategy’ and effective industrial policy. The ...
Debate between Keith Rabois and Zach Weinberg on what tariffs are actually trying to accomplish. One core theme: Tariffs aren’t fully about “bringing back factories,” but rather a negotiation tool to eliminate foreign trade barriers - ultimately aiming to increase free trade, not restrict it.
We also got into:
- What each of them would do if they were in charge
In this freeform episode, Logan sits down with Zach Weinberg (Co-Founder and CEO of Curie.Bio) to break down two of the biggest storylines in tech: tariffs and AI.
They banter through the core arguments for and against tariffs, including national security, domestic employment, and negotiation power. Plus, they revisit what’s happened in past trade wars and share predictions on the real econo...
After unveiling 45 new product announcements this week, Zoom CEO Eric Yuan joined the show to share how he’s thinking about the future of work. He shared how he prioritizes which features to build, his approach to rebuilding company culture, what he’d do differently if he were starting Zoom today, and much more.
(00:00) Intro
(01:14) Eric Yuan on Zoom...
As tariff drama continues to heat up, Ryan Petersen, CEO of Flexport (one of the hottest freight forwarders in the world) came on the show to unpack the impact. Ryan also dives deep into the hidden world of US shipping, opportunities for AI automation in logistics, reflections on building Flexport, and some supply chain conspiracy theories.
(00:00) Intro
(01:16) Flexport's Mission and Operations
(02:28) Impact of Tariffs on Businesses
...
Yamini Rangan, CEO of HubSpot (a $40 billion leader in the CRM space) shares how AI is transforming go-to-market strategies, the key lessons Yamini has learned as a first-time CEO, and the sales tactics she’s mastered.
She also discusses the challenges of navigating major business pivots, including how companies can successfully transition into AI-first businesses and what it takes to stay competitive in an evolving landscape.
(00:00...
Andy is the founder of Artisanal Ventures and Artisanal Talent, one of Silicon Valley’s top search firms. He’s helped build leadership teams at companies like Databricks, Snowflake, Confluent, Abnormal Security, AcuityMD, and many more.
In this episode, he shares…
- How founders can differentiate in the talent war today
- Maximizing the success rate of executive hires
- Why interviews are a waste of time
- The best ways to do references
...
The recent controversy between WordPress and WP Engine put Matt Mullenweg (Co-Founder of WordPress, CEO of Automattic) under intense online scrutiny. In our conversation, he shared lessons from the controversy and managing through crisis, as well as this thoughts on the future of open source AI and more.
(00:00) Intro
(01:17) Controversy with WP Engine
(03:36) Understanding Open Source and Trademarks
(04:36) Automattic's Role and Contr...
Two weeks after Oura CEO Tom Hale started tracking and improving his sleep, he recalls, “It was like walking out of a black-and-white movie into a 4K technicolor movie… I’ve been missing this for 30 years.” The experience of feeling 20 again every day inspired him to apply for the Oura CEO role. Now, nearly 3 years into the job, he sat down to discuss what all founders and CEOs should consider when it comes to avoiding burnout and ...
Jay Chaudhry is the definition of a self-starter. Born in the Himalayas with no running water or electricity until high school, Jay has now scaled Zscaler to a $30B public company. He and his wife went all in many times over—betting their life savings and quitting their jobs to launch their first venture, Secure IT, which became a huge success. Jay then parlayed that into building multiple more self-funded, successful cybersecurity...
In this episode, Marc Benioff (CEO, Salesforce) responds to Satya Nadella’s recent predictions and shares his thoughts on the current reality of Agi. He dives into the rise of digital labor, the multi-trillion-dollar potential of agentic technology, and what the future split between software and agentic revenue might look like. Marc also discusses why CEOs need to stay grounded in delivering actionable solutions, and he emphasizes ...
Eran Zinman entered a crowded category, out-executed everyone, and scaled monday.com into a $14B public company. In my latest conversation with him, he details their unique metric tracking system (dubbed Big Brain) that allows them to do the same amount of work with ½ the people, along with their relentless focus on cash over other metrics, and the little tactics that brought significant ROI (like sending everyone—including investo...
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