Episode 3

Making SMS the #1 revenue-generating channel for e-commerce merchants

Alex Beller
Co-Founder and President, Postscript

Episode Summary

The first SMS message was sent in 1992, but it’s taken a while for messaging to become a standard communication and marketing channel for ecommerce brands. 


Mobile commerce only really took off in the past decade as smartphones and ecommerce were widely adopted by consumers. According to Insider Intelligence, US mobile commerce will nearly double its share of total retail sales between 2020 and 2025.


Postscript is a poster child of the mobile commerce trend. Founded in 2018, Postscript powers SMS for thousands of Shopify stores including brands like Native, Brooklinen, and Olipop. They use Postscript for everything from abandoned carts, to product drops, to 2-way customer support communication.

In this conversation, Chris and Postscript President Alex Beller discuss Postscript’s early days in startup accelerator Y Combinator (YC), where they were in the same cohort as Convictional. Alex shares why SMS has the potential to be a higher revenue-generating channel than email, how brands can leverage it more effectively, and best practices for the upcoming Black Friday Cyber Monday (BFCM) holiday season. Finally, Alex and Chris reflect on the challenges of scaling companies in a remote environment and how they each have grown as young leaders since their time at YC. 


Looking for some more resources to level up your SMS game during BFCM? Check out Postscript’s BFCM Planner here.


Connect with Alex on Twitter and Linkedin

Connect with Chris on Twitter and Linkedin

Check out Postscript

Alex Beller

About The Guest

Alex Beller is the co-founder and President of Postscript, an SMS marketing platform for growing Shopify businesses. Brooklinen, Kopari, Native, and Olipop rely on Postscript for hyper-segmented campaigns and texting with customers. Forbes named his company a Next Billion Dollar Startup in 2021 and has raised more than $106M from top investors like Dick Costolo’s venture firm 01 Advisors, Twilio Ventures, Expanding Capital, m]x[v Capital, Greylock, Accomplice, Elephant, and OpenView. He was previously a Director of Business Development at StackCommerce and received his Bachelor of Arts in both Philosophy and Music from the University of Southern California.

Episode Transcript

Chris Grouchy (00:05):

Hey, everyone. Welcome to season two of the Legends of Retail podcast, brought to you by Convictional. We talk to leaders in retail and eCommerce so you can learn from them about retail strategy, leadership, team management, and take their insights back to your company. I'm your host, Chris Grouchy and president of Convictional. What is Convictional? In short, retailers use Convictional to connect to vendors for drop ship and curated marketplace. My guest today is an eCommerce startup entrepreneur and a very dear friend of mine, Alex Beller. Alex Beller is the co-founder and president of Postscript. After spending years on the brand side of eCommerce, Alex started Postscript to help brands build a mobile-first retention channel. Postscript powers SMS for thousands of Shopify stores, including brands like Native, Brooklynn and Olipop.


They use Postscript for everything from abandoned carts to product drops, to two-way customer support communication and much more. I actually know Alex from our time together at Y Combinator. Postscript and Convictional back in early 2019 were in the same Y Combinator cohort, so I got to see Postscript's early growth very closely, and Alex and I have stayed in touch ever since. In this conversation, Alex and I chat about Postscript's rise to become the defacto SMS messaging platform for Shopify merchants. We also talk about why SMS matters for building stronger customer relationships and Alex's recommendations to eCommerce merchants for this year's holiday season. We get tactical. We also discuss the struggles of scaling our respective companies, the lasting impact that Y Combinator had on us and our respective remote work cultures. Here's my conversation with Alex Beller, co-founder and president of Postscript. Alex Beller, welcome to Legends of Retail.

Alex Beller (02:09):

Thank you, Chris. It's a pleasure to be here on your show, and it's great to see you again. It's been too long.

Chris Grouchy (02:15):

Been too long, and we've known each other for several years now, pretty much since the beginning of both of our respective companies. We were actually in the same YC batch, and in our YC batch there were 205 companies, which at the time was just mind-boggling how, were there even 205 startups in the world, let alone that many in this Winter '19 batch? They split all of the startups in the YC batch into these little subgroups, and I think there are maybe 20 of them or something. We were lucky enough to be in that same subgroup along with a handful of other startups, so we got to know each other pretty well back in those days.

Alex Beller (02:56):

Yeah. That was a lot of fun. I've been reflecting actually, on how well our little group has done from within that batch. There's a whole bunch of heavy-hitting companies from our small group. There was eight companies in there, and I think almost all of them are still kicking and a lot of them are flourishing. There's Gordian and Ashby and us two, I'm missing some, Shef.

Chris Grouchy (03:20):

So many that are just absolutely crushing it in their own respective verticals. But in any case, for most of us in that subgroup, it didn't always look like we were going to survive. I think the one company that was an exception to that was Postscript. I recall very vividly coming to group office hours where we would sit around in a circle and Michael Seibel, CEO of Y Combinator would ask us what you accomplished the previous week. You and your co-founders would always show up and be like, "Yeah, we closed 50K in ARR," and the rest of us are like, "How the heck did they do that?" So I think my experience of Postscript during YC was that you had a lot of strong growth from the beginning. For listeners, maybe let's go back to those YC days. What did you get out of the YC experience?

Alex Beller (04:16):

Yeah. It's funny to hear that from your perspective because I know that that is what we were coming in and saying, but in those days especially, everyone's just so in their own world. We started Postscript thinking that it was going to be a passive side business. We didn't know much about the market we were launching into, and so we thought that we were solving a very specific problem enabling brands on Shopify to send text messages and that this could be a small passive side business, and we'd each make a few thousand dollars a month from it. Right when we launched, we very quickly just saw that pull from the market, and we found product market fit pretty quickly. That first year during which we were NYC and in the small group with you, we saw a lot of growth, and it was really just pull from the market.


It was word-of-mouth, it was in-bound. The YC experience during that I think led to probably a one-and-a-half to maybe two-and-a-half year shortcut in terms of our development in our growth. For us, we'd all worked in tech, but we hadn't come from the most polished or traditional startups. So we were from LA and Phoenix, we didn't have connections to really any investors at all. We didn't know how to think about that process. By going through YC, we were able to move so much faster on fundraising. We were able to learn how that works. We were able to learn so much about just how to orient yourself to the early days of a startup, what to focus on versus not. We got really good coaching from our group partners, especially around not worrying about competition in those early days and just focusing on your customers, because there was a lot of noisy competition back then. All those things together really just led to a huge shortcut in our development.

Chris Grouchy (06:06):

Totally agree with the shortcut in development. As a Canadian, we tend to be less ambitious than our counterparts south of the border. So for us, it was a similar experience of basically having the group partners show us just how big this thing could be and then helping us articulate a path to it. Then everything comes down to execution, so around focusing on customers and growing compounding usage or revenue weekly, those were the things that actually mattered as opposed to all of the noise like competition or even fundraising. Did you have any favorite memories from the batch?

Alex Beller (06:44):

There's a lot of fond memories. There's two that stand out. One was the day we got in, which was the day we went and interviewed. We had no expectations of getting in. All of us had applied and been rejected from YC before for other ideas, and so to be able to get invited to an interview and then we went and we prepared so hard for it, and we walked out of there incredibly confident. We were like, "We think we nailed it." Then to get the call from Tim Brady that night, that was just, it felt like our fortunes had changed just in that one moment. That was the highlight. We were on a train. The other moment that stands out is the other end of the spectrum, which Kevin Hale, who was one of mine and your group partners, we did office hours with him one time.


We knew that he was a design-oriented leader, and so we went to him with some pretty specific design stuff that we were working through, and he just completely scolded us and put us in our place. It was the toughest of love. It was like, "Why are you guys focused on this? You're growing revenue. You have a bunch of customers, go focus on doing whatever it is to increase revenue and learn more from your customers. Stop tinkering with in-app product design." He came down on us so hard over that, that that was a really crystallizing learning moment for us along the way, and definitely a fond highlight as well.

Chris Grouchy (08:15):

It's so interesting you say that because I think we had the opposite interview experience where we just got totally ... our plan, all the preparation that we did, including the 12 or so real mock interviews with YC alumni. Just all of that preparation evaporated within the first 10 seconds of the interview because I think they-

Alex Beller (08:36):

Oh, wow.

Chris Grouchy (08:36):

... caught on to the fact that we were so prepared that they just decided, "Okay, we're going to take a different tact here and just see how they adapt." One of the fond memories was just Michael Seibel asking, "How are you guys going to be a $10 billion company three times back-to-back?" And grilling Roger on his prior answers to tighten it up and use less jargon, be more precise, be simpler. We walked out of there feeling completely defeated despite the preparation that we had done. We got the call from Kevin, thankfully, but agreed on changing of fortunes. Do you remember some of the other ideas that you applied for? I'm curious if maybe you had other experiences that were intense like the ones that we had.

Alex Beller (09:22):

Yeah, so I do remember the other ideas. They were not good, as these things often are. I applied back in the day with an affiliate commerce concept. Are you familiar with the Wirecutter? I worked in affiliate and within eCommerce, and I felt like there was an opportunity to have a whole network, a whole series of incredibly high-end affiliate-driven product review sites in different categories; have one for outdoor gear, have one for parenting and baby products or just category-by-category and didn't even get an email back. Maybe they sent me a rejection email, I don't know. Adam and Colin, who are my two co-founders, they applied with a business that they did. They ran a mobile gaming company, it was called Wiblits, and it had a little bit of traction. It ramped 100,000 users, but they didn't know how to monetize it. This was early days of gaming and they also got rejected for that.

Chris Grouchy (10:26):

All right. Well, one of the beauties of YC is that you can continue to apply and take the lessons as learning and the hard knocks as learning and up your game. But I think the fact that Postscript has done, that did so well out of the gate is telling that perhaps their intuition on picking is actually quite good. I'm curious maybe even to go back before the YC days, dive into the origins of Postscript. SMS wasn't really a brand new technology when Postscript was founded, been around for quite some time. I think the first text message was sent back in 1992, so it's come a long way since, but wasn't certainly a new technology. What was the opportunity that you and your co-founder saw in SMS when you finally got started in 2018? Why do you think that it hadn't already been successful in the world of eCommerce?

Alex Beller (11:26):

The opportunity we saw was fueled by the experiences we were having. It's an interesting question. So what happened was we were working in eCommerce on the brand side of things, not the technology side of things. We were seeing some of the macro trends that are going to sound really old today, but five years ago were maybe interesting, which was that mobile shopping traffic was increasing as a percentage of overall shopping traffic every single year greatly, and desktop had plateaued. At the same time, email marketing performance, at least in the business we were working inside of had plateaued as well. Adam and I, who worked together, were interested in this idea of, "What is going to be the mobile-first retention channel? Is it going to be email? Is it going to be something else?"


Then we had a friend who ran a lifestyle business on Shopify who actually complained to Adam about not being able to text his customers. It was like that was a very specific problem, and at the time, brands weren't sending out texts. Texts had been around for a really long time and maybe a few people would be on Chipotle's SMS list or something like that, but it hadn't been democratized at all. I think that the reason it hadn't is two-fold. One is, though SMS has existed for a long time, most of that has been peer-to- peer and what's called a-to-peer or application-to-peer messaging. A company sending out a million messages at month at once instead of me and you texting one another, that was like ... that's been a newer thing, and additionally, consumers weren't ready for it.


It's taken a long time for actual end consumers to be open to receiving text messages from companies. We get two factor authentication texts from Twitter when we're logging in or whatever, but actually receiving marketing or transactional communication, I think people were very protective of their SMS inbox for a long time. As happens in all messaging ecosystems, over time that protectiveness comes down a little bit, and companies force their way in and slowly things go from weird and new to normal and standard. So I think it's a mix of technology on the messaging side, the ease of use technology being built out with things what we do or what our competitors do, making it easier for marketers to access messaging first developers, and then lastly, and consumers finally being ready.

Chris Grouchy (13:48):

The phone, specifically text messages, seems like such an intimate channel in that if a brand were to rush into that channel and be the first, you could imagine that it would probably be met with a little bit of caution or skepticism from the consumer who's trying to really protect that channel. What seems to have happened over at least the past couple of years is this Cambrian explosion of brands adopting SMS almost all at the same time, and consumers have had really no choice but to accept that this is a way that they can engage with customers. I think one of the interesting things that Postscript is working ... or trying to solve is, "How do we make those text messages conversational so that it's not met with skepticism and disdain?" One of the concepts that I've seen you and the rest of the folks at Postscript really pioneer is conversational commerce. I'm curious if you could break down that concept for our listeners.

Alex Beller (14:47):

Sure. It really is the focus of what we're doing here at Postscript, and what goes into it is that if you look at how marketing has existed on email from a very long time where people are sending out one to many automated communication, everyone's customers are getting abandoned cart messages, everyone's customers are receiving giant, untargeted campaign blasts when a new product comes out or when there's a promotion of some kind. Well, as SMS has become in the mainstream of marketing for eCommerce brands, they've taken and mapped a lot of those email best practices onto text messaging. It makes sense, but what's been missed in that is that actual end consumers interact with text messages very differently than they do with their email inbox. The core thing is we've had an email inbox for a long time where we get promotions in one way newsletters through, text messaging is a two-way system, and people interact with one another back and forth all day long.


So conversational commerce is about building out and enabling two-way use cases native to eCommerce in the SMS thread. To be more specific, things that users normally go to a website to do, maybe it's to place a purchase, maybe it's to initiate a return, talk to support, submit a review, shop around and get more information, we're building a platform that will allow all of those use cases to actually happen natively in the thread so consumers can do those sorts of things without clicking through to a website. That's one aspect of conversational commerce. The other is that conversations don't happen through untargeted blast-based messaging. They happen through hyper-relevant, two-way communication, and so we're trying to set the norm in the market. We're also trying to build technology that makes it easy for brands to have targeted two-way interactions with our customers to go back and forth, to capture information from them, to send them relevant recommendations, to answer questions they have, things like that.

Chris Grouchy (16:45):

It opens up a lot of possibilities for how commerce will change and even new applications of commerce with this channel. What is the theoretical maximum of conversational commerce at Postscript? When you think five, 10 years out, what will the company's products look like? How will it engage with customers or how will your customers engage with their customers? Curious about your thoughts on that.

Alex Beller (17:13):

Sure. I think that we're probably 5% of the way into this transition. Where I would say we are right now is that some of these concepts exist, but very, very, very few brands are adopting the tactics I'm talking about or the approach I'm talking about. I think that's because it's early days of a new marketing channel, there's an arbitrage opportunity just through doing basic one-to-many marketing. So people are making money and that's fine. I think that the theoretical maximum's an interesting question. I think that there's a few different aspects of this.


One is that a user wouldn't have to visit a website to be supported by or interact or complete the entire customer journey with a brand. All of that could happen natively in the messaging thread. The other aspect of this is that consumers will probably only belong to or participate in several text message lists. Probably their favorite brands are the ones who provide the best experience, and through that, they will receive very targeted, relevant automated interactions, which make them feel more like a human commerce interaction like they're having a retail experience at a store than they're in an email drip campaign.

Chris Grouchy (18:23):

It's interesting to imagine a world where the website eCommerce shopping experience no longer exists because it doesn't have to. It's actually inconvenient to go to a URL bar, type in the Google, maybe what you want to buy or find the site of the brand or retailer and then search a giant catalog. You can imagine this world where the brand or retailer initiates the purchase with the customer through text by almost predicting what it is they want to buy, or by simply asking the right questions in the thread and then serving up the right product.


So there's a whole slew of different ways that could be potentially achieved, but there's this website, zero-based purchasing behavior that I think so many brands and retailers would love to get to, especially as the size of their catalogs have to increase in order to compete with the likes of Amazon and other major marketplaces. So if we think a little bit more about mobile post iOS 14 world, this is an area of eCommerce and marketing that I'm less familiar with. But in a post iOS 14 world where first party data has become incredibly important, what role do you think SMS plays for brands?

Alex Beller (19:42):

I think a vital one, and we've seen the market respond that way and validate that, so a couple of different things. The first is that SMS is an owned channel. Whenever a brand starts to build out this marketing asset starts to build their text message list, that's something that they own. It's different than their Facebook ads account in that they own that customer data, they can migrate their list to or from Postscript to any other provider that's an owned asset, and they can reach out to those users whenever they want to once they have the opt-in. That makes them less dependent on external platforms and changing algorithms. The other piece of this is that telephony and SMS specifically is an open protocol similar to email. It isn't a closed-owned network like WhatsApp or Facebook Messenger that you never know what regulation or changes are going to come down, SMS is open.


Those are good things to invest in after getting smacked in the face by iOS 14; however, more specifically to answer your question, and this fits within the conversational narrative that we're seeing and we're exploring is that the brands doing the best work on SMS, they are using this very high engagement channel as a place to capture information about their customers to capture zero-party data. What this looks like is instead of a welcome series saying, "Here's 10% off, buy this, buy this, buy this," it's actually going back and forth with customers in automated conversation, learning about them, gathering preferences, learning if they're men or women, learning what they're interested in, learning what sort of customer they are, holding that data, associating it with the subscriber profile, and then targeting them based on that information moving forward. So the actual ability to capture data back from customers in a text message thread is really powerful, and we're starting to see adoption there.

Chris Grouchy (21:38):

You used a term there that is really interesting, zero-party data. Could you just briefly define what you mean by that and maybe even a couple of examples that, if any, come to mind?

Alex Beller (21:49):

Sure. Zero-party data, which is not something that we created, it is a thing, is essentially data submitted and captured directly from the user. It's not third-party data purchased or targeted against the user, or it's not first-party data that's been purchased by a user, it is zero-party data, meaning data that the user themselves has submitted about themselves.

Chris Grouchy (22:14):

Got it. Okay, and they're volunteering that information?

Alex Beller (22:17):


Chris Grouchy (22:17):

Right. Gotcha.

Alex Beller (22:18):


Chris Grouchy (22:20):

Yeah. I think it's behaviorally you'd probably see very little of customers being willing to provide zero-party data in response to say, an email as opposed to an SMS. That's just a big unlock for brands that are exploring this as a channel.

Alex Beller (22:40):

It is, and we see the performance difference. This isn't rocket science, but if you have more information about a subscriber because you know their gender or because you know why they came to your site or because you know a particular product they're interested in or collection or whatever, you can target them with more relevant marketing and conversion rates go up.

Chris Grouchy (23:01):

Makes total sense. A trend we're seeing in retail and eCommerce is brands setting up third-party marketplaces to basically supplement revenue on their core business. So thinking of one customer that we have, made.com, they make furniture and they basically saw, "Hey look, every time we add a SKU, it just drives tremendous revenue for the business. Let's go explore this in non-competitive categories that really complement the core." I want to somehow tie that back to SMS because this past August, Glossy surveyed 46 fashion and beauty brands, and 37% of them introduced a third-party marketplace to their stores. When you're shipping products from say, third-party brands to your customers, one of the risks is that you dilute your customer experience. Can you speak to how maybe retailers or brands on the Postscript platform are using SMS to create a consistent brand experience for their customers, whether it's through support or intention?

Alex Beller (24:10):

Sure, absolutely. This is a use case we see and we're seeing more of, to your point, and what it comes down to is that this is the most personal communication channel that exists today between brands and consumers. The text messaging inbox is still sacred, and if brands are messaging their customers in there, that's pretty personal space. That means it can be used for better or worse for pretty personal experiences. So what we see the best practice for this use case is is ensuring that it is really leaning into the transactional side of text messaging. So if you're selling third-party brands on your site or through your marketplace, of course, trying to use zero-party data capture to have very relevant messaging and preferences set up in text.


But beyond that, we see a lot of brands utilizing follow ups. What I mean by that is using text messages, not just for marketing purposes, but also post-purchase, post-order delivery to check in with customers to solicit support inquiries if needed to ensure that the quality is there. Just because if a marketplace is drop shipping or even not drop shipping, but just sending out third-party brands, they're probably a little bit less connected to the quality or what the actual customer experience is. Text messaging is a great place to check in with your customers to solicit if any support is needed and ensure that the delivered experience was what they wanted.

Chris Grouchy (25:37):

It is a challenge for these retailers and brands that want to unlock more assortment without holding inventory. I think especially in the world of Shopify, the term drop ship just conjures up these, I don't want to say young people, but they're often very young people trying to get rich quick. Yet, retail executives see it as a very viable business strategy, especially with the backdrop of the current macro environment. We have this challenge of trying to effectively change the stigma around it because of how viable it actually it is when you partner with high-quality brands. But to your point, the retailer still has to take accountability for the customer support through the fulfillment life cycle to the returns in order for it to be successful. SMS sounds like it could be a way to facilitate some of those interactions in a little bit more of a pleasant customer first way.

Alex Beller (26:34):

Definitely, especially for retailers who are maybe a little bit more new to this, I think it's a great way to ensure that you're keeping close to the customer experience.

Chris Grouchy (26:45):

Gotcha. I want to jump to everyone's favorite topic these days, which is the holiday season. Retailers are definitely heads down thinking about this Black Friday, Cyber Monday holiday shopping season. I'm curious about how this might apply to the world of SMS. What are some best practices throughout your years of experience building Postscript, seeing brands be successful with SMS that they can use to apply to really maximize this year's holiday shopping season?

Alex Beller (27:18):

Absolutely. This is going to be my fifth Black Friday, Cyber Monday at Postscript and probably my 12th in eCommerce. It hits different a little every year. There's a few best practices that I would push every single brand towards. The first is, you should be list building aggressively all year, but especially right now, and you shouldn't stop that through Black Friday, Cyber Monday. Oftentimes, those are the highest trafficked days, so even if those users aren't converting, you still want to capture them onto your list. Every branch should be aggressively list building through both on-site pop-up capture, through banners, through keyword in inserts and packaging inserts, at checkout across the board. That's more tactical. The second is on the strategic side. Every well-built SMS program you should ensure going into the holidays that you have non-marketing, post-purchasing automation set up.


I mentioned this earlier actually, but this is checking with customers, ensuring that tracking links are going out, letting them know when packages have been delivered, checking in with them afterward to ensure they're happy with the purchase or if they need any support. Initiating those via text message are great, and it drives down unsubscribes when you also engage transactionally versus just marketing to people all the time. The last tenant of this is, don't be shy. In general, what we see with unsubscribes, and this is something I talk to merchants about all the time is, they don't want to overmarket, a lot of marketers out there are still a little bit nervous about leaning in on the text thread and they don't want to annoy their customers.


What I would say is two-fold. One, the first 30 days that someone spends on your text list are different than the rest. We see that users are five times as likely to unsubscribe within the first 30 days than they are thereafter, which means new people coming onto your list, you want to give them a VIP experience, you don't want to overmarket them. But after that, folks tolerance to receive marketing, especially during Black Friday, Cyber Monday is much higher than you think. So having that mindset of not wanting to overmarket your list, that is the right mindset, but not during Black Friday, Cyber Monday. Don't hold back on text. The unsubscribes will be worth it. As long as folks are outside their first 30 days, you're safe to market to them.

Chris Grouchy (29:34):

Those tactics are pure gold for brands and retailers who are just getting started with this as a channel. I think there are some eCommerce platforms even that make it easy to, or that are very complimentary to the way of thinking about how you market to consumers, giving them a VIP experience. One of those platforms that I think you've aligned very closely to is Shopify exclusively, and other folks in the SMS space are taking a little bit more of a platform agnostic approach out of the gate. Is platform dependency and lock-in a concern for you, or do you think that it makes Postscript the defacto SMS marketing tool of choice for Shopify merchants?

Alex Beller (30:20):

Yeah, that's a good question. I think it's part of why we win, but I don't want us to be there forever. What I mean is what our mission at Postscript is to make SMS the number one revenue channel for eCommerce merchants. That's what we show up to do, and that requires focus. That requires focusing on the channel, and that requires focusing on a specific ICP or customer type. I don't want anyone in the world to be able to use Postscript. I don't want random blogs or non-eCommerce sites or use cases that aren't like native to what we do to want to use Postscript.


I don't want our team to be focused on servicing them. I don't want our engineers focused on building features for them. Instead, I want the product and the experience and the team to be the most knowledgeable and the absolute best at servicing SMS for brands on Shopify. That's why we've started and that's why we focused here, and that pays off because brands will make more money using Postscript than they will a competitor. The flip side of that though is, will we expand beyond Shopify? Definitely. When we feel the time is right, we will certainly expand to some other eCommerce platforms and spread out across some other use cases, but it's still so early in this core one that we're focused on it.

Chris Grouchy (31:34):

Also, there's so much depth to the Shopify platform and the ecosystem that there's probably still a lot of market to grow into, and it probably has ... Well, maybe actually not. You've done very well. You've grown quickly and with that growth you've likely had to think a little bit about how you architect the team and culture. One of the common traits that we discovered about Postscript and Convictional back in our YC days was that we're both remote, and we both do a lot of async stuff. I'd love to learn about what your remote culture is like, and then maybe we can tease out some tactics or recommendations that other companies, both brands, retailers, and even just startups or other types of businesses may have if they want to endeavor to build a successful remote culture.

Alex Beller (32:33):

I'm a little in awe of how you guys are building Convictional. I've read the online manifesto and the guides, which by the way, if anyone hasn't you should, you all have a very particular point of view, which I think probably leads to focus, unity a lot of good stuff. Postscript is fully remote. We've been that way from the start, spread out across the U.S. and Canada. We lean in on asynchronous tooling and asynchronous communication, but we are not an asynchronous company. We actually have a meetings-heavy culture and an alignment-heavy culture. I think that that's a big difference between our two orgs. So we use looms, we write memos, we collab in Google Docs, but there's also a lot of meetings and beyond one-on-ones. There's quarterly kickoffs, quarterly reviews. There's a bi-weekly all-hands. Our management team does an exact stand-up. There's team-level stand-ups, and so I think we're pretty different in that way.

Chris Grouchy (33:31):

Yeah, we try to be minimalistic when it comes to meetings. That has benefits to deep work if you are architecting your calendar for more of a maker schedule versus a manager schedule, which, by the way, for folks listening is an incredible essay from Paul Graham, one of the founders of Y Combinator. But the downside is that it tends to basically create silos at scale. So we see this now that you actually do need some amount of syncing in order to ensure that either work doesn't get duplicated, people aren't feeling misaligned, and that they're actually just working on the right things. I do think that you need to have some meetings, but if you have a meeting on the calendar that just is no longer serving a clear purpose, we advocate for effectively just taking it off the calendar and doing a zero-based budgeting approach to how teams spend their time.

Alex Beller (34:31):

Totally, and I'm very aligned with that. It's actually on my list for as we're starting Q4. I've been reading something interest interesting as well about meeting approvals, which we do not have a micromanagement culture, but I'm not opposed to it that if you're putting a recurring meeting on the calendar, you need department-level approval for it. Postscript's 200 people now. We've sprawled out a bit, but I'm interested in that idea because I think there's meeting creep, and meetings tend to stick around and they take up time, and they get in the way of deep work and focus.

Chris Grouchy (35:03):

Totally. Yeah. The time cost of getting approvals is potentially more expensive than the decision itself. I think maybe we are loosely referencing a similar tweet, but that one did strike me as quite a powerful concept. I want to jump to our last question before we hit you with our rapid fire round. The question is really just about how you've grown as a leader. There's data that suggests that the average age of a unicorn startup founder as 34, guys at Postscript are probably close to a unicorn valuation and you know, started this company in your late 20s. How have you had to mature as a leader over the past four years and maybe speak to some of the challenges that you've faced in scaling as a person, as a human with Postscript's growth?

Alex Beller (36:06):

I'll answer this question, but I want your answer too, because you're on a similar timeline. I want to hear what comes to mind for me is, so just this past weekend, Colin and Adam, who are my partners, we came together to work in person on Sunday and Monday of this last week. It's been a little while since we've done that, just the three of us. So we've been reflecting a lot and as part of that, we give each other feedback, and so these things are top of mind. In every new stage of company building brings just a whole slew of new challenges with it, and I don't think company success is predicated on size of team, I really don't, but I think that size of team is one of the biggest influences on this form of company stage. When you're just the three co-founders, there's very specific challenges.


Then after a while, you probably get used to or good at them. Then there's 10 people and it's a little family, and then there's 25 people and it's a little tribe. Then it's 50 and you have a company. Then it's 150 or 200. It's this thing that's outside of your control and it just exists. The decisions you've made now persist and the norms you've put in place now persist. Each of those stages, for me, has brought a whole set of new challenges and it's required different things, for me, in terms of leadership. It's required me to spend my time differently. It's required me to model different behaviors for the team. What I've found is over the last four or four-and-a-half years, right by the time you start getting comfortable or maybe decent at a stage, you're suddenly dropped into a new stage and you have to learn and calibrate on all these new things and it takes a while.


Some of the specific things that stood out to me from the early days, the biggest was mindset. The feedback that Adam and Colin would give me in the early days was around reacting to things from a place of fear. In business building, there's so much happening outside of your control, and we operate in a very competitive market specifically. We were in YC with you and we were hearing from you guys about big SMS competitors that were going to launch in the space. Clavio had announced that they were going to do SMS, and we were little shrimps who didn't know anything. We were little startup babies, and that stuff was scary for me, and those are some big examples. There's all kinds of little micro examples as well, losing a deal, a partnership falling apart, whatever, whatever all the bumps that you take along the way.


Those things would often rock me a little bit. Maybe we would lose a candidate we really wanted, maybe I would get a little down about them or maybe I would just need to slow down after they happened. It took a while for me to just learn that muscle that actually the trick is anticipating and accepting that there's a million bumps along the way and so much opposition, and you constantly just get punched in the face by the world around you when you're trying to start a company. For me, personally, the trick has been just to learn to enjoy them and anticipate them and let them roll off my back right away, and accept them and focus on the inputs that we are putting into the business into our day-to-day. So getting to a place where I react from place of optimism, that took a little while and that was some hard growth for me.

Chris Grouchy (39:16):

I'm reflecting on my answer now, and because you articulated some of what my answer would've been, and it's interesting because I think our stories are paralleled at the level of learning to develop self-awareness, which has been the greatest gift of being a founder and scaling up and going through tough times and good. I've regretted almost every single conversation or decision I've made when I've been in a state of being reactionary, below the line. One of my favorite books, The 15 Commitments of Conscious Leadership, has this concept at the very beginning of the book called The Line, and you're either above the line or below the line. Being above the line is where you want to be always right. It's curious, open to learning, questioning, acceptance. It doesn't mean that you're just some stoic who's just sitting under a tree, not initiating things in life, but it's basically accepting that things are going to happen without my control or outside of my control, and I need to get really curious about those things and be intentional about the response.


So the greatest learning that seems to be a continuation and something I continue to work on is knowing where I stand in relation to the line, especially in moments where I'm feeling emotional, I'm feeling down, I'm feeling disappointed and taking a step back and working to get myself above the line before reacting. I think that's been one of the single biggest things I've had to work on. Things like therapy, things like giving and receiving performance feedback, like true, cutting performance feedback frequently allow you to accumulate a level of self-awareness that is frankly just difficult to internalize. But the line and being able to locate yourself on the line in those critical moments has been especially key for me.

Alex Beller (41:19):

Totally. That makes me feel some camaraderie with you, by the way. I'll also say that this isn't a challenge for everyone. Growing at different stages is, but people have different strengths and weaknesses. One of my partners, Colin, handles ambiguity and external challenge better than anyone I've ever met. He has other things to grow and lessons learned, but it's been really helpful for me to be able to see that and model some of that.

Chris Grouchy (41:43):

Yeah. I don't know how solo founders do it because the lessons you can learn or the shoulders you can lean on with your co-founders or co-founder can make the difference between surviving and throwing in the towel.

Alex Beller (42:01):

Sure. I have the benefit of also knowing your co-founder, Roger, and I think of you two as pretty brilliant founders who came in with vision and shared skills and interest, but also, you two also bring very different things to the table. I bet you learn from each other constantly, and my bet is that that probably hasn't stopped even though you're four or five years in.

Chris Grouchy (42:23):

Oh, yeah. I think we've just gotten better to leverage each other in situations that will accentuate or call to the other person's strengths. It's like self-awareness, but you also need other awareness and then be able to decide, "Should I be the best person, or am I the right person to make this decision right now, or should I bring in someone else, or does this person actually have a unique take on the situation based on their strengths and lived experience that could make this a sharper decision?" I think that we've just found that we can learn to anticipate each other and bring each other in the right moments. It's actually, I think, led to even shorter syncs between us because we're on the same page naturally, but you've got to get the feedback, especially the cutting feedback, that's the way forward.

Alex Beller (43:19):

It is.

Chris Grouchy (43:20):

Well, I want to jump into our rapid fire round and go through a few of our quick questions. We will give you a question, and I'd love to hear your quick answer on it. How does that sound?

Alex Beller (43:34):

Cool. Sounds great.

Chris Grouchy (43:35):

All right. Most exciting opportunity in retail and in eCommerce?

Alex Beller (43:42):

By far, text messaging, most brands are not doing it. The ones that are are either not doing it super well or are barely started. One of our larger customers, last Black Friday, Cyber Monday, they made more on SMS than they did email, and their SMS list is one 15th the size. The opportunity's gigantic. Gigantic, so definitely that. I know that I'm biased, but definitely that.

Chris Grouchy (44:10):

That's okay, you can be biased. A brand you love and why?

Alex Beller (44:14):

There's a lot of brands that I have real affection for. Let me look and see what's come through recently. Now, you know what? There's two that I'll say. One is HexClad. Are you familiar with them? They're a high-end cookware brand, knives, pots and pans, things like that. I just got my first products from them, and I was really impressed. I'm not a professional chef or close to it, but I've been getting more and more into cooking over the last few years. The weight and clarity and detail that goes into their knives, you can feel, and it cuts very, very well, so that's one. The other I'll say is just a personal favorite of mine. In the pandemic, I got a little into golf and there's a brand called Malbon Golf. They're like a street wear meets golf brand, and they've got some fun stuff that I've been wearing and I've been enjoying.

Chris Grouchy (45:10):

Well, we'll have to get a round of golf together next time we're in each other's vicinities.

Alex Beller (45:16):

Would love that. Would love that.

Chris Grouchy (45:17):

I will be spending a little bit more time in your neck of the woods over the course of the next year. Hopefully, we can make that happen, albeit it'll probably have to be in the summer months.

Alex Beller (45:27):

Please do.

Chris Grouchy (45:28):

All right. Final question here, Alex. The kindest thing someone has done for you?

Alex Beller (45:34):

Wow, that's a great question and a hard one, probably my girlfriend, Caitlin. We've been together since before we started Postscript. As you know, starting any company, and maybe I don't know, starting any company is very intense. Starting a remote tech company in a competitive space is very intense. The way that she's not only allowed me to prioritize my work in the last four years in a way that I hadn't done before, but has also been an active cheerleader of the company and of Adam and Colin and of what we're trying to do I think has required so much from her, and I deeply appreciate it.

Chris Grouchy (46:15):

Well said. I'm sure there's just a lot of kind experiences and examples within that, but it is the selflessness that's coming through is critically important to one's success, selflessness from their partners. I'm sure that's just been an accelerant. Well, what an incredible conversation this has been, Alex. It's always great-

Alex Beller (46:42):

It's been fun.

Chris Grouchy (46:42):

... to chat with you and we will have to eventually do a part two in person maybe before a round of golf, maybe not after. But this has been an incredible opportunity for folks to learn about SMS and how to scale as a leader. Thank you so much for being on Legends of Retail. I've just had a blast talking to you.

Alex Beller (47:03):

Thanks for having me, Chris. It's great to be here.

Chris Grouchy (47:05):

Thank you. Thanks again to Alex for coming on the show, and thank you for listening. To catch the latest episodes of Legends of Retail, please subscribe to the show on Spotify, Apple Podcasts, or wherever you get your podcasts. You can also stay updated by following Convictional on LinkedIn and on Twitter. Finally, if you want to share feedback on the show, I would greatly appreciate it. DM me on Twitter @Chris Grouchy, or you can email me, chris@convictional.com. That's chris@convictional.com. Thanks again for listening.

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