Abadesi talks to Sahil Lavingia, founder and CEO of Gumroad, an online platform that enables creators to sell directly to their customers. Sahil is a very authentic founder who is not afraid to speak uncomfortable truths, as you’ll see in the interview.

They talk about...

* His journey starting Gumroad and what happened when they realized the company wasn’t going to be as successful as they had hoped.

* Why relationships in Silicon Valley are so transactional.

* Dealing with the psychological ups-and-downs of having your identity as a founder so wrapped up in the fate of your company.

* His philosophy of technology, both personally and at Gumroad.

* Why he believes so strongly in in-person connection.

We’ll be back next week so be sure to subscribe wherever you listen to your favorite podcasts. Big thanks to Embroker and Vettery for their support. 

Sahil Lavingia on “failing to build a billion-dollar company”

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On this episode Abadesi talks to Josh Howarth, co-founder of Exploding Topics.

In this episode they talk about...

* His early days as a maker and what he would change if he could do things over again.

* The genesis and evolution of Exploding Topics and the lessons he’s learned through the process.

* How writing updates kept him accountable as a solo founder and his advice for finding a co-founder you can work well with.

We’ll be back next week so be sure to subscribe on Apple Podcasts, Google Podcasts, Spotify, Breaker, Overcast, or wherever you listen to your favorite podcasts. 

How to bounce back as a maker with Josh Howarth

On this episode Abadesi talks to Matthew Paul, software product designer, researcher, and front-end engineer. He’s a former product designer at InVision, he’s worked on software and design systems at IBM, and has designed prototypes at Apple.

In this episode they talk about...

* The open-source design project he’s working on, and how to make good design more accessible.

* Common design pitfalls to avoid and advice for working with designers.

* How he’s working on his personal development and where he learns the most.

We’ll be back next week so be sure to subscribe on Apple Podcasts, Google Podcasts, Spotify, Breaker, Overcast, or wherever you listen to your favorite podcasts. Big thanks to Headspin Mobile for their support. 

Making good typography more accessible and common design pitfalls to avoid with Matthew Paul

On this episode Abadesi talks to Pieter Levels, founder of Nomad List, a global community of international travellers working around the world, RemoteOK, a job board for remote jobs, and Hoodmaps, a unique neighborhood map app.

In this episode they talk about...

* Bootstrapping versus VC, and why he doesn’t want to build a team around his products.

* The difference between creating a website and building a community, and how to think about charging for your product.

* What the future of remote work and the digital nomad lifestyle will look like.

We’ll be back next week so be sure to subscribe on Apple Podcasts, Google Podcasts, Spotify, Breaker, Overcast, or wherever you listen to your favorite podcasts. Big thanks to Headspin Mobile for their support. 

The future of remote work and digital nomadism with Pieter Levels

On this episode Abadesi talks to Waseem Daher, founder and CEO of Pilot. Pilot is bringing bookkeeping into the modern age. He has started (and sold!) two other companies prior to Pilot.

In this episode they talk about...

* The story of starting Pilot and what Waseem learned from his two previous companies.

* When it makes sense to take venture capital versus bootstrap a business.

* How to think about a potential acquisition.

* How Waseem stays productive.

We’ll be back next week so be sure to subscribe on Apple Podcasts, Google Podcasts, Spotify, Breaker, Overcast, or wherever you listen to your favorite podcasts. Big thanks to Headspin Mobile for their support. 

How to get acquired with Waseem Daher of Pilot

On this episode Abadesi talks to Ethan Eismann, VP of Design at Slack. He has previously worked on flagship products at Google, Uber, and Airbnb, as well as at Adobe back when Flash was still a thing!

In this episode they talk about...

* The consumerization of the enterprise and bringing personality to software.

* The design philosophy at Slack and how they use hypotheses in designing their products.

* Customer-centric design and what it means to communicate energy as well as information.

We’ll be back next week so be sure to subscribe on Apple Podcasts, Google Podcasts, Spotify, Breaker, Overcast, or wherever you listen to your favorite podcasts. Big thanks to Headspin, Safety Wing, and Trulioo for their support.

Sahil Lavingia on “failing to build a billion-dollar company”

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