The Startup Playbook Podcast

Insights and lessons from the world's best entrepreneurs and investors

Ep165 – Glenn Rogers (Co-founder & CEO – Float) on focus, constraints & scale

My guest for Ep165 of The Startup Playbook Podcast was Glenn Rogers, the Co-founder & CEO of Float.

Glenn and his Co-founder Lars started Float 11 years ago to solve some of the resource management issues they were seeing through their work at a New York based agency, Razorfish

They tried to raise capital at the start of their journey but were rejected by every VC fund and investor they spoke to, leading them to bootstrap the business and to operate it on the side of their full time roles in New York.

Fast forward to today and Float now employs over 40 people globally and has grown the business to $10M in ARR without external funding.

In this episode we dive into Glenn’s lessons and insights from taking Float from $0 to a $10M ARR business. Specifically we discuss:

  • dealing with well capitalised competitors in a growing market
  • building successful remote first team cultures
  • the importance of constraints
  • evolving the CEO’s role from scrappy startup to scale up
  • and much more!


  • 3:34 – Glenn’s background
  • 4:35 – Lessons from Glenn’s early career at Seek
  • 6:06 – Float’s origin story
  • 8:20 – Managing a FT job and launching/running Float as a side hustle
  • 9:16 – Early plans to raise capital and their adjustment post rejections from VC funds
  • 11:21 – How being forced to bootstrap setup constraints and shifted Float’s strategy and approach to growth
  • 13:59 – Balancing meeting short term needs with long term objectives when working with limited resources
  • 16:00 – Maintaining focus in the face of competition
  • 18:50 – Building effective remote first culture
  • 23:38 – Building trust and connection between remote teams
  • 25:14 – Being hands on as a founder vs hands off as a manager
  • 27:07 – Why Glenn maintained the “head of product” role alongside the CEO role
  • 29:12 – How to judge when to continue or cancel experiments
  • 33:28 – Transition from scrappy startup to scaleup
  • 39:59 – The importance of mentors and advisors

Our partners

A big thank you to Simon Betschel and Josh Ismin for their help with this interview. Also a big thank you to our partners for this episode.


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Links Mentioned 

Glenn’s Links 

People mentioned

Companies mentioned:

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