Mike Seckler is the CEO of Justworks. Maite Diez-Canedo was the CEO & Co-Founder of Via. Via was recently acquired by Justworks to form Justworks International. We cover:

(1:13) - Mike Intro

(1:56) - Maite Intro

(3:08) - How Mike Became CEO of Justworks

(7:17) - How the Idea for Via Came to Fruition

(11:34) - Mike's Relationship with Maite

(13:56) - Maite's Acquisition Experience

(16:40) - Justworks' Synergistic Exercise

(19:16) - Via's Preparation for Justworks Synergistic Exercise

(23:02) - Mike on the Future of HR

(24:43) - Maite on the Future of HR

(27:29) - Maite's Biggest Entrepreneurial Challenge

(32:11) - Mike's Legacy

(35:24) - Maite's Legacy

(36:53) - Mike's Favorite Quote & Most Polarizing Belief

(38:29) - Maite's Favorite Quote & Most Polarizing Belief

Adam is the CEO & Co-Founder at Pitch. We chat about:

(0:34) - Introduction

(2:50) - Adam's Experience at Wunderlist

(7:31) - Starting Pitch With 7 Other Co-Founders

(13:53) - Why Pitch is Different

(18:51) - How To Differentiate In An Existing Crowded Market

(23:00) - How to Inspire Confidence in A Team After Layoffs

(31:47) - Pitch's Moat

(36:31) - The Future of Pitch & Presentation Software More Broadly

(40:05) - Adam's Favorite Quote & Most Polarizing Belief

Michael is the Founder of Houck's Newsletter and Megaphone. We chat about:

(0:47) - Introduction

(2:21) - Michael's Experience Working at Uber & AirBnB

(4:55) - Michael's Community-Based Businesses

(7:28) - Comparing Newsletter Businesses & Traditional SaaS

(10:30) - Why Michael Removed ~15,000 Newsletter Subscribers

(13:50) - Which Metrics Newsletter Founders Should Care About

(16:37) - Starting a Newsletter From Nothing

(22:01) - Why Struggling Newsletters Are Probably Struggling

(23:41) - Michael's Thoughts on Newsletter Frequency

(26:10) - Michael's Latest Venture - Megaphone

(29:50) - What No One Talks About That Kills Most Startups

(33:44) - Michael's Most Polarizing Startup Belief

Allan is the CTO of Webflow. We chat about:

(0:33) - Introduction & Background

(1:43) - Planning For Rocketship Scale

(6:02) - How Important it is to Have Customers Early On

(7:25) - How Operating at an Early-Stage Startup Framed VC Lens

(9:21) - Can VCs Have a Sole Finance Background?

(10:56) - Working With Tobi Lütke & Stewart Butterfield

(13:58) - What Attracted Allan to Webflow

(16:37) - What Allan's Learned at Webflow

(17:43) - B2C Vs. B2B Customers

(19:49) - Future of Web Development & Webflow

(22:01) - Webflow's AI Thoughts & Plans

(25:03) - Allan's Advice For Younger Developers

(30:30) - Allan's Favorite Quote

Gino is the CMO of DailyPay. We chat about:

(00:28) - Background & Introduction

(1:47) - Why Gino Chose Marketing

(3:40) - DailyPay Marketing Team

(7:04) - What DailyPay Enables

(13:34) - DailyPay's Business Model

(14:46) - Best Marketing Tactics

(16:58) - Thoughts on AI

(19:37) - Future of On-Demand Pay Space

(22:40) - Favorite Quote

Shay is the CMO of ActiveCampaign. We chat about:

(3:19) - What a CMO Actually Does

(8:42) - Using Design as a Mechanism to Solve Problems

(16:35) - Design, Marketing, Product... Which is Most Important?

(18:29) - ActiveCampaign's Moat

(23:11) - What People Don't Understand About AI in Marketing

(30:50) - Future of Email Marketing

(40:55) - Favorite Quote & Most Polarizing Belief

Ross is the CEO & Founder of ZenBusiness. He was also the founding CTO at HomeAway, the vacation rental company that sold to Expedia for $3.9B. We chat about:

(1:28) - Introduction

(3:16) - How Ross Got Into Tech & Startups

(5:36) - Neuro-Lingustic Programming

(7:20) - Best Way to Validate a Business Idea

(14:23) - Expedia's Acquisition of HomeAway

(17:18) - Transitioning From CTO to CEO

(25:09) - How ZenBusiness Knew What to Build First

(30:14) - ZenBusiness' Moat

(33:55) - What People Disagree With Ross on

Malte Ubl is the CTO of Vercel. We chat about:

(2:00) - Ease of modern technology & AI/LLMs

(6:23) - How Vercel's thinking about providing the best UI/UX

(9:49) - How Malte inspires a high velocity culture at Vercel

(14:18) - How Vercel sets itself apart

(16:08) - Differences between working at Google & a startup (Vercel)

(19:44) - Malte's thoughts on the open & closed source landscape

(27:59) - Products Vercel has brought to startup customers

(30:53) - Incremental or failed migrations

(33:28) - Vercel's spaces product

(39:17) - Where Malte/Vercel thinks the industry is going

Vivien Garnès is the Co-founder & Co-CEO at Upfluence. We chat about:

(1:01) - Introduction & founding story of Upfluence

(3:32) - Upfluence's biggest source of growth

(8:53) - Why influencer marketing is so effective

(17:45) - Marketing channels complementary to influencer marketing

(21:33) - Why Upfluence isn't a two-sided marketplace

(24:55) - Upfluence revenue breakdown

(29:39) - Upfluence analytics

(34:30) - What's next for Upfluence & influencer marketing

As the Co-founder and CEO of Cameo, Steven's learned a lot about building a lasting consumer business. We chat about:

(1:18) - Cameo's founding story

(6:23) - Signs of prospective entrepreneurs

(11:07) - Building a consumer marketplace, overcoming cold start problem

(18:22) - Steven's Favorite Cameo

(21:59) - Cameo for business & Cameo for kids

(27:43) - Cameo's Moat

(30:47) - Talent owning their audience (not renting)