In Depth

Latest Episodes:

From a narrow ICP to a wide-open market – Lessons from Webflow’s Bryant Chou on using customer empathy to get product-market fit Mar 09, 2023

Show notes

Todd Jackson is back on the mic to guest host another product-focused episode this week. He chats with Bryant Chou, co-founder and founding CTO of Webflow, a no-code visual web design platform built with freelance designers and developers in mind.

Today, Webflow is valued at over $4 billion and has millions of users all over the world. More than 200,000 freelancers, agencies, small businesses and enterprises use Webflow to help design and power their websites at businesses large and small.

But Webflow didn’t always market to such a wide customer base. In our conversation today, Bryant rewinds the clock to Webflow’s early days — when it was just a co-founder team of three building a better tool to design a website.

We explore why the Webflow co-founding team had such a strong conviction that designers were their ICP, and why they took much longer to launch than other folks in their Y Combinator cohort. Bryant also explains how Webflow wrangled their viral launch on Hacker News into a sustainable revenue and shares his root cause analysis framework for collecting customer feedback.

On the surface, Webflow’s path to product-market fit seems incredibly smooth. But as Bryant tells it, there were plenty of bumps in the road — and he’s got tons of advice for early-stage founders that are finding their footing.

How to lead with transparency amidst adversity — Don Faul, CEO of CrossFit and former Google, Facebook & Pinterest exec Feb 23, 2023

Show notes

Our guest today is Don Faul, CEO of CrossFit.

Don has a fascinating background where he’s been able to find success in environments as different as a combat zone and a corporate board room. After spending 8 years as a platoon commander in the U.S. Marine Corps, Don had stints at some of the most vaunted companies in tech, including Google, Facebook and Pinterest, the latter of which he served as the Head of Operations. It’s a really unique set of leadership experiences spanning very different cultures.

In today’s conversation, he answers some burning questions like if micromanagement is always a bad thing, how to create a long-term company vision that genuinely gets people fired up about the future, and what folks tend to get wrong in their all-hands meetings.

We also discuss what it takes to lead in this current environment, and how leadership looks different when things feel like they’re going off the rails, which plenty of startup folks are feeling right now. Don unpacks his biggest lessons on how to embrace transparency when things aren’t going well, and candidly shares his own experience of having to wind down a company.

Read the article Don penned for First Round Review: The Pivotal Stories Every Startup Leader Should be Able to Tell.

You can follow Don on Twitter @donfaul

You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

From kickoffs to retros and Slack channels — Stripe's documentation best practices with Brie Wolfson Feb 09, 2023

Show notes

Our guest today is Brie Wolfson.

Brie spent nearly 5 years at Stripe, where she worked on bizops and launched Stripe Press, followed by a stint at Figma where she worked on education. She then started her consultancy, named The Kool-Aid Factory, to share her lessons on building team cultures. And now she’s operating as a first-time founder building Constellate, a new productivity and communications tool for teams.

In today’s conversation, we’re focused on company culture. A decade or so ago, companies like Google and Amazon dominated the cultural zeitgeist, with founders wanting to emulate their secret sauce. Today, there’s a newer guard of companies that startups want to model themselves after, with Stripe at the very top of the list.

Brie peels back the layers into not just the cultural pillars that drove Stripe’s meteoric rise, but also how these showed up in day-to-day work.

We also zoom out beyond Stripe to talk about her work teaming up with companies with The Kool-Aid Factory, seeing culture and company-building up close. Brie shares advice on codifying your operating principles, establishing meaningful rituals, and growing this kernel of culture as the company scales.

Read the full essay Brie recommended during the interview: Reality has a surprising amount of detail and the article she penned for First Round Review: Ditch Your To-Do List and Use These Docs to Make More Impact.

You can follow Brie on Twitter @zebriez

You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Why comms deserves its own spot on the exec team — Aaron Zamost’s lessons from Square Feb 02, 2023

Show notes

Our guest today is Aaron Zamost.

After a comms career at Google, Aaron joined Square in 2011 to lead corporate communications. He went on to join the exec team, reporting directly to Jack Dorsey and leading the comms strategy for Square’s IPO in 2015. In an interesting move, he also took on leading the people organization as well, running both orgs up until he left in late 2020. In addition to lecturing at UC Berkeley's School of Law, Aaron now runs Background Partners, a communications consulting firm.

In today’s conversation, we dive deep into what founders need to know about both external and internal comms. Aaron shares more on:

Why comms deserves its own spot on the exec team and why most founders shouldn’t hire PR agencies.
The jobs-to-be-done of the comms function in the early days of a startup — and why it’s not a good customer acquisition strategy.
A 3-question framework for simplifying your company message early on.
How to prep for interviews and deal with difficult lines of questioning.
How to think about commenting on events in the news, or message layoffs to the team.

Given how much the media landscape has changed in recent years, and how many founders are grappling with internal comms issues these days, Aaron’s advice makes for a valuable listen.

We also recommend checking out his two excellent Medium posts:

-What’s Your Hour in ‘Silicon Valley Time’?

No, you don’t need to hire an agency

You can follow Aaron on Twitter at @zamosta. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.

What founders need to know about acquisitions: Shopify’s Daniel Debow on M&A lessons from selling three startups Jan 26, 2023

Show notes

Our guest today is Daniel Debow, a VP of Product for Demand at Shopify.

Daniel is a three-time founder and a seasoned M&A pro. Daniel oversaw the process of all three of his companies’ acquisitions and has helped continue to grow them at scale inside larger corporations. His most recent startup, Helpful, was acquired by Shopify in 2019. Before that, he co-founded Rypple which was acquired by Salesforce in 2011. His first startup, Workbrain, was acquired by Infor in 2007.

In our conversation today, we focus on all the moving parts of running an M&A process as a startup . Daniel shares tactical advice on:

What conditions founders should look out for at potential acquirers, as well as what established companies can do to create a more “founder-friendly” environment
How to spot clear buying signals and weed out companies that are just “tire kicking”
How to build meaningful relationships with executives of all types, not just corp dev teams.
Techniques for including your investors in the M&A process, as well as messaging tips when opening up about the process to the wider team.

You can follow Daniel on Twitter at @ddebow. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.

How to build your culture like a product — Lessons from Anna Binder, Asana’s Head of People Jan 20, 2023

Show notes

Our guest is Anna Binder, Head of People at Asana.

We go back to the earliest days when Anna first took on the role, starting with how she prioritized the initial things to tackle as a new People exec and combing through a slew of opinions that bubbled up from other folks at the company.

Next, she shares her tactical playbook for creating a culture of feedback for not just low-performers, but high-performers, too. Anna also unpacks her methodology of conscious leadership, and how the best leaders always interrogate how the opposite might be true. She shares her insights from working on Asana’s executive team for nearly 7 years, and how to build habits to make sure this group is a healthy nucleus at the center of the company.

We end with a rapid-fire round, with some quick hits tackling onboarding, all-hands meetings, and mentors.

You can follow Anna on Twitter @annaebinder.

You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

How to scale your career alongside your startup: Mike Boufford’s lessons after 10 years at Greenhouse Jan 12, 2023

Show notes

For our first episode of 2023, our guest is Mike Boufford, CTO of Greenhouse, an applicant tracking system and recruiting platform.

Mike has a unique career as an engineering leader. He wrote the first line of code at Greenhouse in May 2012, and he’s still there — over a decade later. This isn’t the typical path of non-co-founding engineers, who usually get layered or leave to start their own ventures.

In our conversation today, we focus on how founders build an environment that makes early employees want to stay, and importantly, how leaders can build the career skills and self-awareness they need to succeed at a startup long-term. Mike shares more on:

How his own motivation changed over time and how he managed his relationship with the company’s co-founders.
The techniques he used to prepare himself for every next phase of growth and how his role would have to change in 18-24 months.
Why he read two books on every other executive’s area of the business when he joined the leadership team.

Mike also refers to his First Round Review article in the interview, which we definitely recommend reading: Why This Engineering Leader Thinks You Shouldn’t Aim for Zero Regrettable Attrition.

You can follow Mike on Twitter at @mboufford. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.

Founders: Here’s how to get your sales pitch in ship-shape — Peter Kazanjy Dec 15, 2022

Show notes

Our guest is Peter Kazanjy, co-founder of Atrium and author of “Founding Sales: The Early Stage Go-to-Market Handbook.”

As an early-stage founder, there’s something comforting about the build stage. You’re tinkering with the nascent product, honing your MVP and dreaming up the possibilities of how much folks are going to love what you create. But once you get out of that comfort zone of quietly building and start trying to sell, things tend to get infinitely more complicated.

In today’s conversation, Pete lays out the roadmap for getting founder-led sales right in the early days. From small exercises to build up your selling muscles, like his “turbo rapport” challenge to thornier topics like self-diagnosing if your selling narrative is working, he’s got tons of advice for breaking down the art of a sales call. Pete also shares tailored guidance for folks who are facing the additional hurdle of creating a new category (and trying to create a new budget), with the playbooks he used building Atrium.

You can follow Peter on Twitter @Kazanjy. Check out his articles for First Round Review, including his lessons on building a customer advisory board.

You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Deepak Rao on how X1 pivoted, launched, built a +600K-long waitlist and fundraised in tough times Dec 08, 2022

Show notes

Todd Jackson is back on the mic to guest host another product-market fit focused episode this week. He chats with Deepak Rao, co-founder and CEO of X1, a consumer fintech startup that’s building a credit card for a new generation.

Just last week, X1 announced a $15 million funding round. But we’re here to rewind the clock and unpack how the startup got to this point. As you’ll hear in today’s conversation, the path required a dramatic pivot. Here’s a preview of what Deepak shares:

The emotional journey of how the pandemic forced them to abandon the initial idea for a personal loan product.
How the team validated demand for the new idea by focusing on the launch announcement and getting all of the branding exactly right — before building anything.
The launch strategy that crashed X1’s website and built up a 600K long waitlist. .
Why finding product-market fit is different for consumer companies, plus advice on fundraising in tough times.

Whether you’re in the early innings of starting a company, going through a tough pivot yourself, or planning out your product’s launch there are tons of helpful tactics here.

You can follow Deepak on Twitter at @drao1. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @tjack.

How to lower barriers to change when building and selling products — Jonah Berger’s advice for founders Dec 01, 2022

Show notes

Our guest today is Jonah Berger, a marketing professor at the Wharton School at the University of Pennsylvania and the bestselling author of “Contagious” and “Invisible Influence.”

Today we’re chatting about his follow-up book, “The Catalyst: How to Change Anyone’s Mind.” Founders start companies to change industries and behaviors, but change is hard. Going back to chemistry, Jonah notes that catalysts don't just create change by pushing harder or exerting more energy — they remove or lower the barriers to change. (In the book Jonah offers a helpful framework about 5 specific barriers to change, called REDUCE — which stands for reactance, endowment, distance, uncertainty, and corroborating evidence.)

We focus on how founders and leaders can do that in the context of building and selling products. Jonah shares his thoughts on:

Whether you truly need to build a 10X better product and why a startup’s biggest competitor is actually inertia.
The role of urgency in selling or getting someone to adopt a product.
How to apply the freemium approach in different contexts, like with physical products.
Techniques for negotiating price, as well as the role that identity and category creation play in persuasion and product adoption.

You can follow Jonah on Twitter at @j1berger. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.

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