VC Corner Q&A: Madison McIlwain of Defy VC

The Startup Grind Team
Startup Grind
Published in
6 min readNov 17, 2020


Madison McIlwain is an Associate at Defy, where she works alongside her team to source, invest in, and help amazing companies grow. She’s passionate about retail innovation, supply chain, and consumer technology.

Formerly a product manager at Gap Inc, Madison managed a team of over forty engineers to modernize Gap’s order management system and customer communication channels. There, she drove numerous technology initiatives, such as enabling SMS communication for customers and launching the first website-wide chatbot. Before Gap, Madison worked at Rent the Runway and an AI start-up working to create a shoppable virtual closet.

Read on to learn more about Defy’s mission and the most important question Madison asks herself before committing to an investment!

— What is Defy’s mission?

Being an entrepreneur means questioning everything. It means pushing back on all the smart, well-meaning people who tell you you’re wrong. At Defy, our mission is to help entrepreneurs Defy convention and expectation. We’re an early stage venture firm focused across consumer, enterprise/saas, and deep tech. We love people who are positioned to uniquely disrupt the industry they’ve grown up in. We hope to back and empower the next generation of startup leaders who defy all odds and build impactful, enduring companies.

— What was your very first investment? And what struck you about them?

The first investment I sourced for Defy was Thrilling. Thrilling is bringing vintage retailers online and enabling consumers to shop vintage from the comfort of their home — all while enabling more sustainable shopping and the circular economy. Honestly, I was drawn to the founder, Shilla, and her magnetic energy and passion for the problem. Shilla herself is an avid vintage shopper who wanted a better experience finding vintage treasures online. She’s built a marketplace that supports small businesses and reduces waste on our planet by leveraging technology to digitize thousands of single SKU items. From my time at Gap and Rent the Runway, I knew SKU management for resale was very challenging and believe Shilla will be the one to turn these challenges into scalable solutions.

— What is one thing you’re excited about right now?

I am really excited about the circular economy and how technology is enabling a more sustainable supply chain. I explored this in detail recently here. When I was at Gap, return rates were better than the average but still sad. What most customers don’t realize about returns is that they are unprofitable and unsustainable for retailers in a myriad of ways. Retailers lose on shipping items back and forth. They also lose on the restocking labor. Worst of all, retailers usually have to mark down inventory once it’s returned to them because it’s often no longer in season. Returns are a side effect of a burgeoning ecommerce ecosystem. With innovation in reverse return logistics and end of clothing life management, we have an opportunity to disrupt the returns status quo.

— Who is one founder we should watch?

Kimberly Shenk! I want to be Kimberly when I grow up! Not only is she a kick butt founder as CEO of Novi Connect, but she is also a thoughtful, compassionate and kind person. With Novi, she is powering ingredient and supply chain transparency. Consumers are increasingly demanding transparency around what’s going into all of the products they touch, eat, wear, etc and the many companies that make/sell all of these products are struggling to deliver. Novi’s software solves this problem through a SAAS-enabled network. I’ve learned a lot from her by the way she breaks down big problems into small manageable pieces and works her way back to a solution.

— What are the 3 top qualities of every great leader?

  • Tenacity
  • Humility
  • Kindness

— What is one question you ask yourself before investing in a company?

The question I always ask myself is “would I invest my own savings into this business?” If the answer is no, it’s a signal to me I don’t have enough conviction on the product, market, or team.

— What is one thing every founder should ask themselves before walking into a meeting with a potential investor?

What is one key objective I’m hoping to get out of this meeting? It might be funding. But more often than not a first meeting is a stepping stone to establishing a relationship with that investor and firm. Capital may come, but this person might be helpful in other avenues as well; customer introductions, hiring, or connections to a more suited firm.

— What do you think should be in a CEO’s top 3 company priorities?

  • Building product and culture
  • Hiring great leaders
  • Retention both of customers and employees

— Favorite business book, blog or podcast?

Is it cheating if I say my podcast? The Room is a podcast with your favorite founders and founders where we discuss what it was like to be in The Room where it happens. Our target audience is first-time founders and young funders. My co-host, Claudia Laurie and I are both curious digital natives navigating our careers in the Valley asking the same questions as our listeners. We felt there was an opportunity to bring to life the conversations and the creation stories which historically happen behind doors closed to groups across age, gender and race. If you like How I Built This, our podcast is for you!

— Who is one leader you admire?

Sally Gilligan. Sally is the CIO of Gap Inc. Sally gave me my first job as a product manager in Gap’s supply chain. At our company all-hands and during our one on ones, she taught me both how to command a room and make an individual feel worth listening too. She continues to lead Gap Inc. through a compelling digital transformation with her keen insights for where the future of retail aided by technology is heading.

— What is one interesting thing most people won’t know about you?

Most people wonder how I have so much “energy”! I think it baffles people because it’s pretty relentless and honestly sometimes I exhaust myself. I think my energy comes from being an extreme extrovert. I genuinely derive the most energy when I’m around others. Thankfully, in venture, my job is to talk to people which consistently fuels me, hence the energy.

— What is one piece of advice you’d give every founder?

Lean into curiosity and stay determined to build a better experience for your customers.

Ready to make a pitch? Startups looking for an opportunity to pitch Defy or other great funds can apply here!



The Startup Grind Team
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