Tech, Tactics, and Takeovers with Claire Milligan

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7d ago 43:10

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“Don’t stop being that person who steps off the ledge.”

In this episode, Michael Dargie connects with Claire Milligan, founder of Aimably, whose career has evolved from a designer obsessed with user experience to an entrepreneur helping businesses navigate private equity transformations—without losing their soul (or their engineers).

This episode is sponsored by my new book BRANDJITSU, helping you find, shape, and share your story with the world.

Claire shares her journey from building products inside a small startup to leading business lines within private equity–owned companies. When rising AWS cloud costs became immovable obstacles, Claire and her colleague Mark founded Aimably to solve one very expensive problem: making cloud hosting costs understandable—and manageable.

She breaks down how cost and engineering decisions in tech are often misaligned, how the traditional gross margin model fails modern SaaS, and why firing developers to improve numbers is not the solution. There’s also time for farting Santas, sourdough alternatives, and Claire’s favourite ski patrol memories in Lake Tahoe.

This conversation dives deep into systems thinking, entrepreneurial grit, and why people—and their quirky personalities—are what drive the best businesses forward. It’s candid, funny, and packed with aha moments about building better companies and better lives.

Quotable quotes

“We do margins wrong in software.” —Claire Milligan

“People are just the beginning and the end of the conversation.” —Claire Milligan

“Don’t stop being that person who steps off the ledge.” —Claire Milligan

“We get stuck in decisions that have cascading consequences.” —Claire Milligan

“You had me at farting Santa.” —Michael Dargie

Episode highlights

Aimably’s Mission | Helping businesses navigate private equity with cloud cost clarity

Cloud Reality Check | Why AWS bills forced Claire into entrepreneurship

From Logo Design to UX | Claire’s design roots lead her into tech

Obsessed with Cars | User experience goes beyond screens

Grandpa’s Farting Santa | Corporate leadership meets absurd desk décor

Needlepoint Sass | Claire’s unexpected creative outlet

Software ≠ Car Manufacturing | Why tech doesn’t track costs like physical goods

Redefining Margins | Putting engineering up top changes the math

Broccoli, Reimagined | Life (and vegetables) after the 80s

On Chairlifts and Wisdom | Claire’s ski patrol reflections

Baking Through Burnout | Croissants, millionaires shortbread, and pandemic therapy

Leisure Isn’t Just for the Rich | Why Great British Bake Off matters

Around the World in Two Weeks | A father-daughter adventure

Rebel Advice | When you step off the ledge, stay authentic

Links from episode

Aimably Website (https://www.aimably.com)

Claire Milligan on LinkedIn (https://www.linkedin.com/in/clairemilligan)

BrandJitsu Book (https://brandjitsu.com)

Hosted by: Michael Dargie THEREBELREBELPODCAST.COM | LINKEDIN.COM

Get Your Copy of Michael's Book: "BrandJitsu™: Move Your Brand From 'Meh' To Memorable" Indigo | Barnes & Noble | MichaelDargie.com

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