I've Been In eCommerce Long Enough To Know Who(m?) To Ask

Aaron Schwartz

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MARKETING
UPDATED WEEKLY

Each week, I'm sitting down with the most interesting people in eCommerce - founders, investors, marketers, and agency leaders who are actually doing the work. We're skipping past the highlight reels and getting into the real stories that shaped their success.

16H AGO

How to Make Big Bets When You Have No Idea If You’re Right, with Kyle Hency and Rishabh Jain

In this episode, Aaron Schwartz (Orita.ai), Rishabh (Fermat), and Kyle Hency (GoodDay Software) have a candid conversation about their entrepreneurial journeys, building companies, and navigating the evolving commerce tech landscape. They discuss their approaches to team building, hiring strategies, and the impact of AI on business operations. Timestamps: 00:48 - Introductions and background of all three founders 06:00 - Rishabh explains why he started Fermat and being "wrong about everything" 09:23 - Kyle discusses his transition from Chubbies to founding GoodDay Software 17:24 - Discussion on different approaches to gathering customer feedback and signals 20:43 - Challenges of bringing teams along during rapid growth and testing 28:30 - Kyle's approach to hiring for deep industry context 31:40 - Rishabh's unique hiring philosophy for finding the best talent 36:44 - How they balance advisory roles while running their own companies 42:06 - The transformative impact of AI on internal operations and business leverage 49:51 - Final thoughts on product-market fit and fundraising advice

53 min
MAR 5

While You're Obsessing Over Email, Your Competitors Are Mastering This Emerging Channel

In this episode, Aaron Schwartz discusses email marketing, Klaviyo, SMS strategies, and cross-channel marketing with three agency experts: Jess Grossman (InSocial), Kolby Yarnell (Modular), and Sammy Tran (BMO Media). They share practical insights on Klaviyo's pricing changes, SMS segmentation, cross-channel attribution, and the future of lifecycle marketing. Timestamps: 00:00 - Introductions 03:41 - Klaviyo Pricing Changes Explained 09:36 - Cross-Channel Marketing Strategy 20:30 - SMS Segmentation Best Practices 27:12 - Email vs. SMS Opt-in Strategies 29:45 - Measuring Incrementality Across Channels 36:06 - Attribution Challenges for Agencies 39:38 - Future of Lifecycle Marketing & AI Tools 46:46 - RCS Messaging and Future Trends These lifecycle marketing experts cover how to properly segment your list, maximize ROI across different channels, and prepare for upcoming changes in customer communication technology.

49 min
FEB 26

Why You Need To Start Leaving a Little Mystery With Your Customers, with Peyton Fox, Lenin Batista, and Gabrielle Pitman

When Klaviyo announced their pricing changes, my LinkedIn feed exploded with hot takes and panic. But here's the thing: after sitting down with three of the sharpest minds in ecommerce - Gabrielle Pittman, Lenin Batista, and Peyton Fox - I'm more convinced than ever that this shift is an opportunity. What struck me most was how quickly our conversation moved from 'How do we cut costs?' to 'How do we create better customer experiences?' Lenin shared brilliant insights about using Klaviyo's APIs to intelligently suppress and unsuppress customers based on their buying cycles. As he put it, if you have a jewelry client whose customers buy once a year for anniversaries, does it make sense to email them at day 180 or 270, or should you wait for the full year? Then Gabrielle dropped what might be my favorite insight of the conversation: Sometimes your best customers need breathing room. Just because someone spent $13,000 on your product doesn't mean they want to hear from you every day. In fact, that might be the fastest way to lose them. The real gold came when we started talking about alternative channels. Direct mail – yes, actual physical postcards – emerged as an unexpected hero. I'll admit it: I recently bought a rug because of a well-timed postcard. It sat on my counter, caught my eye at the right moment, and boom – sold. Sometimes the "old school" approaches still work magic. (Shoutout, Revival Rugs!) Peyton brought it home with practical tips on segmentation and engagement, emphasizing that it's not just about who you remove from your list – it's about identifying who you might be overlooking. As Lenin pointed out, the days of batch-and-blast are pretty much over. (And yes, I'll admit to being guilty of that approach on Mailchimp back in the day). What became clear through our discussion is that successful email marketing isn't about saving money – it's about driving profitable growth. If you're optimizing for a smaller Klaviyo bill, you're solving the wrong problem. The real question is: How do we send the right message, to the right person, at the right time?

48 min

3 Episodes

Each week, I'm sitting down with the most interesting people in eCommerce - founders, investors, marketers, and agency leaders who are actually doing the work. We're skipping past the highlight reels and getting into the real stories that shaped their success.

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Aaron Schwartz
Years Active

2K
Episodes

3
Rating

Clean
Show Website

I've Been In eCommerce Long Enough To Know Who(m?) To Ask

I've Been In eCommerce Long Enough To Know Who(m?) To Ask

Episodes

How to Make Big Bets When You Have No Idea If You’re Right, with Kyle Hency and Rishabh Jain

While You're Obsessing Over Email, Your Competitors Are Mastering This Emerging Channel

Why You Need To Start Leaving a Little Mystery With Your Customers, with Peyton Fox, Lenin Batista, and Gabrielle Pitman

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