In Depth

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37 reviews
This podcast has
61 episodes
Date created
Last published
Average duration
60 min.
Release period
14 days


Welcome to In Depth, a new podcast from First Round Review that’s dedicated to surfacing the tactical advice founders and startup leaders need to grow their teams, their companies and themselves. Hosted by Brett Berson, a partner at First Round, In Depth will cover a lot of ground and a wide range of topics, from hiring executives and becoming a better manager, to the importance of storytelling inside of your organization. But every interview will hit the level of tactical depth where the very best advice is found. We hope you’ll join us. Subscribe to “In Depth” now and learn more at

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From PM to VP of Product: Jiaona Zhang’s career advice from Webflow, Airbnb & Dropbox
For our 60th episode, we’re doing things a little bit differently — with a new guest host! Welcome to Todd Jackson, who’s filling in for Brett Berson this week. Todd is also a Partner at First Round, and the episodes he hosts will mostly focus on product, given his previous product roles, from the VP of Product & Design at Dropbox and Director of Product Management at Twitter, to being a PM at Facebook and Google, leading Newsfeed and Gmail. He was also a founder — his startup Cover was backed by First Round in 2013 and later acquired by Twitter. (For more on Todd and his advice for company building, check out his article in The First Round Review from a couple years ago.) Today, Todd chats with Jiaona Zhang, the VP of Product at Webflow. (She goes by JZ though, so you’ll hear that throughout their conversation.) You might remember her popular Review article, Don’t Serve Burnt Pizza (And Other Lessons in Building Minimum Lovable Products) Before joining Webflow, JZ was the Senior Director of Product Management at WeWork, a Product Lead at Airbnb, and a PM at Dropbox and at Pocket Gems, a mobile gaming company. JZ also teaches product at Stanford and mentors a lot of rising product leaders, so she’s the perfect person to talk to about building a career in product. As the framework for the entire conversation, we start with why she doesn’t think of it as a career ladder, but rather as three distinct phases: contributing as a PM, managing PMs, and then leading the function. Here’s a preview of what Todd and JZ cover: The PM role. Advice on breaking into the function, what you should look for when you’re a candidate interviewing for PM roles, and the mistakes that are easy to make early on. The managing phase, including how to think more strategically as you get more senior, archetypes to look for when hiring, and her advice for first-time managers.  The executive phase. JZ talks about thinking of your org as a product, and she shares super tactical pointers for working with your CEO, your peers on the exec team, and the board. Whether you’re trying to break into product, grow in your career, or you’re a founder looking for hiring advice, there’s tons in this conversation for you. You can follow JZ on Twitter at @jiaonazhang. You can email us questions directly at or follow us on Twitter @firstround and @tjack.
“When They Win, You Win”: Russ Laraway unpacks his new guide for the modern manager
Today’s episode is with Russ Laraway, a seasoned leader who's been at Google, Twitter, Candor Inc, Qualtrics, and is now the Chief People Officer for Goodwater Capital Since we last had Russ on the show, he’s written a new book, titled: “When They Win, You Win.” On today’s episode, we dive deep into the management frameworks and original research that Russ discusses in his book. He starts by pointing out how broken our process for selecting managers is to begin with, where we often default to just promoting the highest performer on a team, rather than looking for folks who explicitly demonstrate leadership chops. He explains the raw ingredients that point to whether someone’s ready to take on a management role — even if they weren’t the best individual contributor of the bunch. And if you’re looking to hire a manager from outside of the company, he’s got plenty of interview questions to suss out the right hire. Next, we explore the heaps of research that Russ did in writing this book, and how that led to him pulling together a few specific frameworks for managers to lean on. This includes a list of the behaviors of highly-engaging managers — and how you can put these into practice. As Russ discusses in today’s interview, there are countless resources out there on how to be a better manager — often with tons of conflicting advice. Russ distills all of this down to an essential, research-backed guide for the modern manager that cuts through the noise. You can follow Russ on Twitter at @ral1. His book, “When They Win, You Win” comes out on June 7, 2022. You can email us questions directly at or follow us on Twitter @ and
Building a highly-technical enterprise product? Essential advice for product leaders — Nate Stewart of Cockroach Labs
Today’s episode is with Nate Stewart, CPO of Cockroach Labs, the creator of database product CockroachDB. In today’s conversation, we cover his essential advice for building a highly-technical product. He sketches out how the Cockroach team decided on the specific use case for its database product. Nate explains the steps the team took to reach conviction on their go-forward plan — which meant saying no to a lot of customers who didn’t align with the product roadmap. Nate dives into the tactical ways to avoid taking on too many customer commitments, which he calls tech debt for product teams. Next, Nate dives into his advice for approaching design partnerships, especially when handling more conservative enterprise clients. He explains the different types of design partners, and why you should have all of those represented in the early days of your startup. Finally, we wrap up with his advice for other product leaders, including how to create a rock-solid partnership with a CEO as the first head of product, and how he solicits honest feedback across the executive team. You can follow Nate on Twitter at @Nate_Stewart You can email us questions directly at or follow us on Twitter @ and
Building & selling a product into government is tricky — Phaedra Ellis-Lamkins shares critical advice for getting it right
Today’s episode is with Phaedra Ellis-Lamkins, co-founder and CEO of Promise, a modern government payment solution. In today’s conversation, Phaedra explores the ins and outs of selling a product into government. Phaedra pulls back the curtain of how she and the Promise team tackle the extra-long sales cycles, navigate layers of subcontractors, and convince risk-averse decision-makers to take a chance on a startup. We also take a step back to traverse the winding road that led to Promise in its current form. Like plenty of founders before her, Phaedra had to pivot her way into product-market fit. She explains the signals that the first iteration of the product, a bail reform platform, wasn’t going to work as she’d hoped. She then doles out lessons for other founders in the process of pivoting. You can follow Phaedra on Twitter at @phaedrael You can learn more about our advertiser Cocoon at You can email us questions directly at or follow us on Twitter @ and
The art of starting a startup — Gagan Biyani’s advice for generating, validating, and executing on ideas
Today’s episode is with Gagan Biyani, co-founder and CEO of Maven, a company that empowers the world’s experts to offer cohort-based courses directly to their audience. After being early at 3 startups that achieved over $1 million in run-rate in their first six months of going live, Gagan has learned some valuable lessons and seen a wide range of outcomes — from Udemy going on to IPO in 2021, to Sprig shutting down in 2017. In our conversation, we dive deeper into the process of starting a startup. We start on generating ideas and open-ended exploration. We talk about key signals to look for in the market and the competition, as well as the mistakes he sees many aspiring founders make. Next, he recaps his concept of minimum viable tests for validating early versions of your idea. As we mention in the episode, Gagan wrote a popular article on The First Round Review last year, where he shared much more detail about his “Minimum Viable Testing Process.” Then, we dig into how you start bringing the idea to life, from exploring different potential business models, to selecting your co-founders and managing that relationship as the company grows. If you’re eager to hear even more on finding startup ideas from Gagan, he’s teaming up with The Hustle’s Sam Parr to run an Ideation Bootcamp on the Maven platform — learn more and sign up here by May 2nd if you’re interested. You can follow Gagan on Twitter at @gaganbiyani. You can email us questions directly at or follow us on Twitter @firstround and @brettberson.
How to handle comp challenges at every startup stage — Kaitlyn Knopp’s advice from Pequity, Instacart, Cruise & Google
Today’s episode is with Kaitlyn Knopp, founder and CEO of Pequity, which automates HR workflows to make compensation more equitable and scalable. Prior to starting Pequity, Kaitlyn built compensation programs and teams at companies like Instacart, Cruise, and Google — bringing a deep well of experience to this often complicated topic. We start our conversation with her advice on the traps founders need to avoid when they’re making their first hires. She sketches out a lightweight framework of how to think about comp at this early stage, from broad levels to an initial comp philosophy. We then get into the pros and cons of negotiating offers, as well as creative approaches you can bring to other aspects of comp outside of salary, such as the exercise window. Kaitlyn also shares tons of tips around how to communicate the value of equity, especially with candidates who’ve never worked at a startup before. In the back half of our conversation, we dig into the comp challenges that come up as a company starts to grow quickly. Kaitlyn shares advice on retaining existing employees through techniques like equity refreshes. We also get into the psychology of bonuses, as well as how to navigate inflation and salary adjustments. Kaitlyn shares her take on the recent trend of offering very individualized packages, and she ends on the importance of helping employees to fully understand their comp, and not shying away from topics like dilution and tax considerations. You can follow Kaitlyn on Twitter at @KaitlynKnopp. You can email us questions directly at or follow us on Twitter @firstround and @brettberson. For more information on Cocoon, visit
A crash course on comms for founders — Nairi Hourdajian’s early-stage advice from Figma & Uber
Today’s episode is with Nairi Hourdajian, the VP of Communications, Content and Community Marketing at Figma. Prior to joining Figma, Nairi was the Chief Marketing Officer at Canaan, an early-stage venture capital firm. In 2013, she became Uber’s first communications person and spent the next 3 years building out the function. Before getting into tech, Nairi came from the world of politics. She was a VP at Glover Park Group, a communications consulting firm started by former Clinton officials, and she also served as a policy director for the Democratic Senatorial Campaign Committee and as a staff assistant to then-Senator Joe Biden. Our conversation focuses on what a great communications strategy looks like at early-stage startups. Nairi breaks down the basics for founders who aren’t familiar with this function, and shares advice for thinking beyond just announcing your Series A funding. She shares lots of thoughts on crafting foundational messaging for different audiences and shaping the company narrative — with examples from both Uber and Figma, as well as startups she’s advised. Next, we get into the nuts and bolts of building relationships with reporters. Nairi shares her take on handling negative stories about your competitors, and offers tons of tactical pointers on how to prepare for a media interview. We ended on her advice for assembling the team that can help you shape and execute on your comms strategy — from working with agencies and freelancers, to making your first full-time comms hire. You can follow Nairi on Twitter at @NairiHourdaj. You can email us questions directly at or follow us on Twitter @firstround and @brettberson.
How founders can get executive hiring right from startup to scale — advice from Lattice’s Jack Altman
Today’s episode is with Jack Altman, co-founder & CEO of Lattice. There were so many topics we could have gotten into with Jack as it relates to scaling as a founder and CEO, but we decided to dive deep on executive hiring, a huge challenge for founders.  The conversation starts with how the hiring profile for executives changes as the company grows. Jack is a strong believer that you should focus on hiring someone who’s a great fit for the next 18-24 months, not the next 5 or 10 years. (Here's the blog post he mentioned about the different stages a CEO faces.) He also talks about the traps of hiring “too big,” whether that’s over indexing on BigCo experience, or focusing on seniority and titles that don’t match your startup’s current challenges. Instead, Jack shares more about why founders should focus on getting good at assessing and taking a chance on more junior, undiscovered talent.  Next, we dig deep into his end-to-end hiring process, from how he sources folks and what he asks in interviews, to why he sometimes does references on a candidates’ references. Whether it’s diving into how a leader might build out their team, or the red flags that signal that an executive candidate doesn’t have an ownership mentality, Jack shares tons of tactical pointers. We also get into where executive hiring errors come from, as well as the leading performance indicators to look for and what to do when a new executive leader doesn’t work out. We end by chatting about promoting internally versus hiring externally, and why you should think about your executive team like you’re constructing a portfolio. You can follow Jack on Twitter at @jaltma. You can email us questions directly at or follow us on Twitter @firstround and @brettberson.
IC? Manager? Technical Founder? How to chart your engineering career path — Stripe & Cocoon’s Amber Feng
Today’s episode is with Amber Feng, who is the co-founder and CTO of Cocoon, and was previously an engineering leader at Stripe for eight years. In today’s conversation, we pull on threads from Amber’s engineering career to weave together lessons for other engineers charting their own path. Although Amber’s spent the majority of her career at Stripe, she’s had all sorts of different experiences — from individual contributor, to engineering manager, to heading up entire orgs, and then back to individual contributor again. We begin by discussing the unexpected traits that differentiate the most high-achieving engineers up and down the org chart. We also get into the debate that most engineers face during their career — whether to hone your craft and become an expert IC, or go the management route. Amber’s gone back and forth between the two, and shares the advice she gives to other folks who are considering where their strengths may be best leveraged. Finally, we turn the page to the most recent chapter in her career journey — becoming a first-time founder. She shares the lessons from Stripe’s Patrick Collison that she’s applying to her own company Cocoon and shares words of wisdom for other engineers with interest in starting their own company from 0 to 1. You can follow Amber on Twitter at @amfeng You can read the First Round Review article Amber mentioned with the co-founder questionnaire here: You can email us questions directly at or follow us on Twitter @ and
Never done sales before? Meka Asonye shares GTM playbooks from Stripe, Mixpanel, and backing founders at First Round
Today’s episode is with Meka Asonye, a Partner at First Round Capital. This week marks the one year anniversary since he joined, making the transition from seasoned GTM leader to full-time early-stage investor. Prior to First Round, Meka served as the VP of Sales & Services at Mixpanel, where he ran the more than 100-person global revenue team and owned the customer lifecycle from first website visit to renewal. Meka also spent four years at Stripe as it scaled from 250 to 2000 people and matured its sales org. When he first joined in 2016, he served as one of the payments company’s early account executives, leading their first attempts to go upmarket and land enterprise logos. For the next three years, he headed up Stripe’s Startup/SMB business. In today’s conversation, Meka starts by digging into his playbook for founder-led sales, from what a great first customer conversation looks like, to how to self-diagnose what went wrong. He also shares advice for founders making their first hire, including the leveling mistake that’s easy to make, and what to ask in the interview and in reference calls. He also offers thoughts on comp and the leading indicators to look for after onboarding. We then dig into structuring early pilots, from what makes for a good design partner, to how to make sure your ICP is well defined enough. We also cover helpful tactics for customer success, which Meka finds is often the most overlooked aspect of go-to-market. Throughout the conversation, we also touch on how Meka’s experiences have translated into his first year as a VC. We end on his advice for startup folks looking to transition into venture. To read more of Meka’s go-to-market advice for founders, check out his article in the First Round Review:  You can follow Meka on Twitter at @BigMekaStyle. You can email us questions directly at or follow us on Twitter @firstround and @brettberson.
The startup playbook for expanding internationally — Advice from Faire CEO Max Rhodes
Today’s episode is with Max Rhodes, the co-founder and CEO of Faire, an online wholesale marketplace that connects independent retailers and brands. Prior to starting Faire in 2017, Max spent several years at Square, where he was a founding member of Square Capital, the first product manager on Square Cash, and a Director of Consumer Product for Caviar. In today’s conversation, we dive deep into how startups can get international expansion right. After launching in the U.K. and Netherlands in March 2021, Faire company expanded into countries like France, Germany, Italy and the Nordic region. They’re now in 15 markets, with over 700 employees in 10 offices around the world.  After sharing the company’s origin story and initial strategy, Max offers a helpful analogy that helped him decide when to go international, and details some lessons he learned from other companies like DoorDash and Airbnb. Next, Max takes us through the nuts and bolts of how the Faire team approached their first international launch, from staffing and operations, to how they thought about local competitors. Max also walks us through the operating cadence and strategic planning process that powered Faire’s international growth. We also talk about the human side of scaling internationally, and the growing pains that come along with it.  To help mitigate the effects, Max shares how he’s implemented the concepts from the First Round Review article on “Giving away your Legos.” Read the article here:  You can follow Max on Twitter at @MaxRhodesOK. You can email us questions directly at or follow us on Twitter @firstround and @brettberson.
Usage-based? Hybrid? Tiered? Which pricing model is right for you? — Stripe’s Jeanne DeWitt Grosser
Today’s episode is with Jeanne DeWitt Grosser, Head of Americas Revenue and Growth for Stripe, where she’s responsible for all sales functions and leads the company’s enterprise strategy. She joined Stripe after a career in sales at Google and also serving as Dialpad’s Chief Revenue Officer. In today’s conversation, we dive super deep into all things pricing. To start, Jeanne outlines the trade-offs when it comes to usage-based pricing versus SaaS pricing, and how usage-based gets your company more closely aligned with the customer. She also debates the merits of hybrid or tiered pricing that Stripe has implemented and provides tips for other companies looking to go this route. Next, she explains her philosophy of treating pricing like a product, and how this shows up in Stripe’s org design. Jeanne outlines some of the pricing experiments that have had the biggest impact on how the company does business, and her tips for getting a steady drumbeat of customer feedback. To wrap up, she shares her advice for founders when it comes to treating pricing as an art and a science. If you’re in sales, or are a founder just starting to think about pricing your product, you won’t want to miss Jeanne’s insights she’s picked up over the course of her career. She’s got plenty of ideas for small startups and larger companies alike. Along the way, Jeanne provides plenty of examples from her time at Stripe to illustrate her playbook in action. You can follow Jeanne on Twitter at @jdewitt29 You can email us questions directly at or follow us on Twitter @ and

Podcast Reviews

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4.9 out of 5
37 reviews
Rivers aaaaa 2021/09/19
Insightful and practical
Love this podcast - wonderful to listen to and a lot of takeaways!
TinnaAcorn 2020/11/03
Immediately applicable
Really enjoyed this. Brett asks the best questions and Molly shared great tips from her career. I’m going to rethink how we can help people lead witho...
AlexM40 2020/10/30
Wow. First round has one of the best newsletters out there and this podcast is living up to that reputation. Keep up the great work.
tasha-xo 2020/10/29
Excited for this
If your other content initiatives are any precedent, this podcast will be ? Excited to listen. -Damir @ Index


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