40 Minute Mentor

September 27, 2023

Bootstrapping to Exit & Disrupting B2B Sales, with Nick Telson, Co-Founder of Trumpet

Today’s 40 Minute Mentor is Nick Telson, exited Founder of DesignMyNight, Co-Founder of Trumpet, Angel Investor and Podcast Host of the popular Pitch Deck show.

With so many hats to wear, we loved diving into Nick’s story and career from starting at L’Oreal to scratching that entrepreneurial itch by building DesignMyNight to 100+ employees with minimal angel funding and finally returning to the Founder seat to disrupt B2B sales.

There is SO much to unpack from Nick’s impressive story, from his views on failures to what it really feels like to exit and start again, and so much more…

“Becoming financially free but not being a Unicorn, is still success.”

Nick Telson

Tune in to discover

Having ‘failure moments’ and the glorification of entrepreneurship [02:37]

The idea of DesignMyNight from the streets of NYC [06:46]

From side hustle to exit [10:55]

Advert: More about JBM [18:13]

Round 2 of Founder life: Trumpet’s origin story [19:21]

Being VC backed and hiring principles [22:17]

Building in public and fundraising journey [23:52]

Fundraising advice [34:35]

Hiring advice for securing your initial team [37:09]

Applying to and joining Trumpet [39:50]

Audience question: Making the startup world more inclusive [42:25]

Listen on

Helpful links

➡️ Connect with Nick: https://www.linkedin.com/in/nicktelson/

➡️ Find out more about Trumpet: https://www.sendtrumpet.com/?ref=linkedin

➡️ Listen to Pitch Deck: https://www.nicktelson.com/podcast

Enjoyed this episode?

Keep up to date with all our latest episodes, by hitting the subscribe button on your favourite podcast platform. And for any feedback on what you enjoy the most and ideas on what we can do to make 40 Minute Mentor even better, please leave us a review.