The Shopify Mafia

July 21, 2023
Tech Mafias

Company "mafias" are all the rage, and we here at PIN love to dig deep into the most influential 'Tech Mafias,' especially since we're huge on democratizing access to startup investing by supporting communities with all the legal and bureaucratic work when it comes to setting up a community investment club.

This week we take a look at the top companies from the Shopify Mafia. So far, a total of 54 companies have been founded by former Shopify employees, and a total of $262 million raised. Below we cover companies that have raised the most money, as well as rising stars.

If you missed our previous posts, make sure to check the Twitter Mafia, Lyft Mafia, Stripe Mafia, Netflix Mafia, InstaCart Mafia, Dropbox Mafia, Revolut Mafia,Tesla Mafia,Square Mafia, Reddit Mafia, VMware Mafia, Amazon Mafia, SpaceX, Slack Mafia, OpenAI, Google Mafia and Pinterest Mafia articles. Investing in fellow coworkers' startups, especially as a community or alumni group, is one of the best ways to get in early on deals as well as support the ideas and ventures of people you love and admire. Who knows what's around the corner in your own network and community!

Companies covered:

  • Envoy
  • Win Brands Group
  • BookClub
  • Cover
  • Fixie AI
  • Highbeam
  • Order
  • Delphia
  • Freedom Robotics
  • Fuzzbuzz
  • Maple
  • Creator Now
  • Trexity


Founder: Larry Gadea
Shopify Role: Systems Performance Advisor
Capital Raised: $170.2M
Investors: Menlo Ventures
Stage: Series C

Larry is the CEO and founder of Envoy. They have a small, but growing startup based in SOMA in San Francisco, CA. Their focus is to encourage modern engineering and elegant design on often-neglected, yet highly-visible workplace systems.

Win Brands Group

Founder: Taylor Sicard
Shopify Role: Partner Manager
Capital Raised: $90M
Investors: Oaktree Capital Management
Stage: Series B

Taylor is the co-founder at Win Brands Group which is a portfolio of owned and operated brands including Qalo, Homesick, and many others. Taylor also co-founded Uptime which gives proactive alerts about issues on your Shopify online store.


Founder: Ada Pally
Shopify Role: Digital Marketing Manager
Capital Raised: $26M
Investors: GSV Ventures
Stage: Series A

BookClub is a virtual book club platform that provides an new way for readers and writers to connect and discuss books.


Founder: Anand Dhillon, Karn Saroya, Natalie Eva Gray, Ben Aneesh
Shopify Role: Developer, Product
Capital Raised: $27M
Investors: Y Combinator
Stage: Series B

Cover is a modern purveyor of insurance, focusing on making property insurance fair and accessible for members across the US.

Fixie AI

Founder: Zach Koch
Shopify Role: Director of Product Management
Capital Raised: $22M
Investors: Bloomberg Beta
Stage: Seed

Zack has a background in computer science with a focus on HCI. He is the co-founder at which is an automation platform for Large Language Models.


Founder: Gautam Gupta
Shopify Role: Software Engineer
Capital Raised: $17M
Investors: FirstMark Capital
Stage: Seed

Gautam is the co-founder of Highbeam, which helps ecommerce brands be more profitable by giving them real-time cashflow insights, a flexible line of credit, and no-fee banking that saves you money where you spend the most.


Founder: Tom Jaklitsch
Shopify Role: Software Engineering Intern
Capital Raised: $44.7M
Investors: Collaborative Fund
Stage: Series B

Tom is the co-founder and CTO of Order. Order is a guided B2B marketplace with a mission to simplify buying for businesses. Order makes it easy for businesses to place and track purchases across all their vendors, control spend, and make payments in a single, consolidated bill.


Founder: Andrew Peek
Shopify Role: Director of Product Labs
Capital Raised: $79.5M
Investors: Ribbit Capital
Stage: Series A

Andrew is the co-founder and CEO at Delphia which is building the world's first investment strategy that anyone can improve with their data.

Freedom Robotics

Founder: Dimitri Onistsuk
Shopify Role: Head of Marketing
Capital Raised: $6.6M
Investors: Initialized Capital
Stage: Seed

Dimitri is the co-founder and COO at Freedom Robotics. It is the leading provider of software infrastructure for modern robotics companies. Based in San Francisco, California, Freedom Robotics creates mission critical software infrastructure to enable the next generation of robotics companies to build, operate, support and scale robots and robotic fleets.

Rising Stars


Founder: Everest Munro-Zeisberger
Shopify Role: Developer Intern
Capital Raised: $2.9M
Investors: Y Combinator
Stage: Seed

Everest is the co-founder and CTO of Fuzzbuzz, which lets dev teams test their code 24/7 for security vulnerabilities by making fuzz testing dead simple.


Founder: Mike Taylor, Michael Perry 
Shopify Role: Senior Lead of Engineering, Director of Kit
Capital Raised: $3.5M
Investors: Inspired Capital
Stage: Seed

Mike is the CTO and co-founder at Maple. Previously he was also the CTO and co-founder at Kit, which is a virtual marketing assistant for business owners.

Creator Now

Founder: Zack Honarvar 
Shopify Role: Sales Representative
Capital Raised: $3M
Investors: Upfront Ventures
Stage: Seed

Zack is the co-founder and CEO at Creator Now, which is reimagining film school for the creator economy in order to help more people actualize their dreams of becoming a content creator!


Founder: Alok Ahuja
Shopify Role: Operations Director for Experts Marketplace
Capital Raised: $6.4M
Investors: Jason Myers
Stage: Seed

Alok has been working for 15+ years in software technology and e-commerce. He is the Chief Executive Officer and co-founder of Trexity, an on-demand ‘last mile shipping’ logistics solution, from beginning to end.

Join our waitlist
Love what we do? Give us a follow on: