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Haley Kwait Zollo is Principal at Starting Line, a Chicago-based, thematic early-stage venture capital fund focused on investing in consumer services and products that are cheaper and better. They’ve invested in companies like Cameo, Catch Co, SpotHero, and many more.

Before joining Starting Line, Haley was VP of Strategy and Business Operations at Mac & Mia and was Manager of strategy and analytics at Trunk Club. She began her career as a Transaction Services Associate at KPMG.

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Here’s a glimpse of what you’ll learn:

  • Haley Kwait Zollo shares why she turned down a job offer from Cameo and opted to join the Starting Line team instead
  • Haley was to help build out analytics at Cameo, so she talks about what that means for any business
  • Key analytics metrics to look at in a marketplace businesses like Cameo
  • How Haley helped build out the analytics for Trunk Club
  • Important KPIs to measure and build efficiency around when running a business
  • Why are early-stage investment deals very competitive right now?
  • What Haley and Starting Line looks for before they decide to invest in a company
  • Companies Haley has worked closely with at Starting Line
  • Haley’s most important advice to early-stage startups on how to have non-linear growth
  • Areas where new categories of technology-driven businesses are emerging
  • Haley talks about the challenges that came with building and cultivating relationships digitally and a high point in her career so far

In this episode…

Building a business in today’s highly digitalized world is a double-edged sword because there’s a lot of data created that can make or break a business. The misanalysis of data or analyzing the incorrect data can lead to poorly informed decision making that can hurt your business. But on the flip side, using the data and measuring KPIs the right way will drive important decisions that can multiply your business’s growth.

However, the million-dollar problem is how do you know which metrics to measure and how do you identify which KPIs move the needle for your business?

On this episode of Inspired Insider, Dr. Jeremy Weisz interviews Haley Kwait Zollo, Principal at Starting Line, about the importance of making informed decisions in business. They discuss Haley’s background in analytics, her foray into the VC world, the data and KPIs digital brands should be analyzing, and Haley’s advice to early-stage startups on how to have non-linear growth. Stay tuned.

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Episode Transcript

Jeremy Weisz

Dr. Jeremy Weisz here, Founder of where I talk with inspirational entrepreneurs and leaders. Past guests, Haley I always like to give a shout out to the Chicago based companies to past guests include Ross Gordon, who is founder of Catch Co,. and Mystery Tackle Box which we’ll definitely talk about SpotHero I had on the podcast Jeremy Smith, one of the co-founders that was fantastic. Dan Zawacki started Lobster Gram he was shipping live lobsters in the mail in the 1980s. And a few years ago, sold his company that and many more check out and check them out other episodes on Before I introduce today’s guest, this episode is brought to you by Rise25, which I co-founded with John Corcoran. We help businesses give to and I like to say Haley connect to their best relationships, you know, by helping you launch and run your podcast. For me the number one thing in my life is relationships. I’m always looking at a way to give to and profile the people I admire the people I love what they’re doing, and putting them front and center stage in their company. And I’ve done that over since 2008 through podcasting, so you can check out If you or your company have thought about starting launching a podcast. We’ve been doing it for a long, long time. And you know, before I introduce to you, Haley, I have to give a big thank you to Leslee Cohen, who’s Principal at Hershman Cohen. She helps companies who are raising money. And she does so much more than that when I was talking to Leslee, I didn’t realize early on, she has this fascinating experience that she helped companies going through IPOs like early on in her career. So it was fascinating to hear that so you can check her out at and I’m excited. Haley Kwait Zollo is Principal at they made investments in companies like Cameo, Catch Co which I mentioned SpotHero many more. And she was you know, previously was working with Trunk Club and KPMG. So she’s got a wide range of experience in all types of companies. So Haley, thanks for joining me.

Haley Kwait Zollo

Thanks for having me, Jeremy. Excited to be here.

Jeremy Weisz

We’ll talk about the journey. how you got into Starting Line previously, but let’s start with Starting Line. People can check it out How did you meet Ezra and Ade?

Haley Kwait Zollo

Yeah, so it’s funny connection actually. So a couple different ways. The the startup I was at most recently, prior to Starting Line was called Mac and Mia, it was a clothing service for children. And one of our investors was Chicago Ventures, which was where Ezra was before Starting Line. So I kind of always knew him, I thought he had a really cool style. He was doing these awesome consumer deals, SpotHero was actually a deal that he did while at Chicago Ventures. And I just really admired what he was doing. And I was just following him. So it’s funny because my husband’s actually an entrepreneur. He was at GrubHub and left started one company about five years ago. And he was not working within the Chicago VC ecosystem him and Ezra kind of headed off, and then, you know, serendipitously when I was at Mac and Mia, Ezra reached out to grab coffee, and we had a conversation, he was trying to recruit me to go to Cameo, which was the deal he had just did. And I kind of flipped the script on him. And I said, Hey, you know, I’m trying to see what the startup is gonna do. I’m think it’s a little bit premature, but I love what you’re doing. I think it’s really awesome that you’re starting a brand new VC here in Chicago with this consumer thesis and venture is always something that has been on my long term roadmap and just curious, you know, what the job is like and wanting some exposure, so let me know how I can help you out. And we kind of left it at that and he was really receptive. So for about five, six months, we were just exchanging emails, you’re getting coffee, I was helping due diligence on the sideI met Ade who was the first venture party partner he brought on? And you know, the Mac and Mia story was very winding but it came to a situation where we sold the company and I was ready to make my next move. And I said, Hey, Ezra, you’re the first conversation I want to have. And would love to be part of the Starting Line team. So came on board officially in the summer of 2019. And about a year and a half in I’m like, so blessed and so excited for where I’ve been and everything I’m learning and having a blast so far.

Jeremy Weisz

So Haley, what did he want you doing at Cameo, so he was trying to recruit you? What did he want you to do?

Haley Kwait Zollo

So this was you know, back then and by the

Jeremy Weisz

way, if anyone has not heard of Cameo They should check it out. It’s It’s amazing. It’s terribly addictive, unfortunately. So I will go on and I’m like, Oh, you know, 30 minutes later, I’m looking through other celebrities. So I mean, just mention a little bit like Cameo does. And then maybe What did he want you to do there?