Engineering Founders

In this episode, we cover bootstrapping & transitioning from side gig to full-time, featuring Darian Shimy, Founder @ FutureFund. He shares the origin story of FutureFund and how his children’s school experience inspired the company’s mission & product goals. He shares valuable tips on dealing with anxiety, betting on yourself, setting expectations, and making decisions as a founder. We also dissect how to iterate on your core marketing message & test pricing strategies throughout the different phases of FutureFund. Plus, considerations for scaling, fractional work engagements, hiring, and organization structure.

ABOUT DARIAN SHIMY

Darian Shimy is the visionary founder and CEO of FutureFund Technology, an innovative platform designed to streamline fundraising and sales for K-12 school groups. With a robust background of over 25 years in web technologies and engineering team management, Darian has held key leadership roles at notable companies including Square, Weebly, and eHarmony.com. He holds an MS in Computer Science from The University of Southern California and maintains a passion for coding in his free time. Outside of his tech career, he dedicates time to coaching youth sports, in both recreational and competitive teams.

"I feel like I'm doing an experiment and the experiment is this, what if you can get a fraction of time from the best people you've ever worked with in your entire life? Some could be 10 hours, some could be 30 hours, some could be 20, whatever it is, but like the best designer, the best product, the best engineer, the best salesperson, the best whomever, and pull them in to help out on a short amount of time. It has allowed us to grow at a pace that I think is sustainable for us and allows us to focus on quality.”

- Darian Shimy

ABOUT FUTUREFUND

FutureFund streamlines fundraising and selling for school groups! FutureFund is a digital platform that provides powerful tools for K-12 school groups and PTAs for fundraising, growing membership, financial reporting, and communicating with volunteers—all in one clean, user-friendly interface.

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SHOW NOTES:

• Staying customer-focused while working toward the future @ Samsara (3:22)
• Merging forward-looking technology & customer-problem-focused product-building conversations (5:54)
• Defining customer success & working backwards from winning (8:38)
• How stage gates can confirm / assess feature accuracy & maturity (10:58)
• What the approval moment looks like while moving from stage to stage (15:29)
• Understanding what stages offer the greatest opportunity for risk / friction (17:11)
• Signals to watch for that allow you to move forward with confidence (19:30)
• Best practices for anticipating & preparing for future possibilities (21:13)
• Using smaller-scale projects to inform future direction of larger-scale products (23:12)
• Communication strategies for working with less technical stakeholders (25:22)
• Methods for effectively communicating complex, technical information (27:59)
• AI / ML team composition at Samsara (30:04)
• Frameworks for aligning & motivating folks to focus on customer needs (32:59)
• Strategies for introducing new technologies & scientific research into your teams (35:06)
• Introducing AI into mission-critical internal tools (36:34)
• Rapid fire questions (39:17)

LINKS AND RESOURCES

• Holly - Holly Gibney, one of Stephen King’s most compelling and ingeniously resourceful characters, returns in this thrilling novel to solve the gruesome truth behind multiple disappearances in a midwestern town.

This episode wouldn’t have been possible without the help of our incredible production team:

Patrick Gallagher - Producer & Co-Host

Jerry Li - Co-Host

Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/