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Sippin' & Shippin'

Episode 42: Disruptive conversations: A midyear look back

Sippin' & Shippin'
Sippin' & Shippin'
Episode 42: Disruptive conversations: A midyear look back

Tanya Phipps|June 23rd, 2023


We’re midway into 2023 and hosts Brian Weinstein and Caitlin Postel are taking a look back at the year so far.  We’ve had some incredible guests visit the podcast, who are disrupting e-commerce challenges and sharing their wins. Listen to how they are adapting nimbly and boldly through the ever-changing wave of consumer demands, post covid. Also hear the team highlight some of the most dynamic moments, while sharing a bit of their own advice along the way.


1:00     What’s Jackie Robinson got to do with this?!

2:54     Why a little disruption, can be a good thing

4:54     That new approach in the returns space

7:31     Key takeaways from a VC capitalist and investor

9:17     WHM highlights

12:44   The digital transformation is here: Insights from a master

15:11   Meeting customers where they are, but how?

16:54   The business of personalization, how things have changed

20:09   “Variation is the enemy of automation,” that’s the quote!

21:56   The state of ecommerce: looking ahead

24:50   Some lasting advice for all the entrepreneurs out there


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Brian Weinstein: Welcome everybody to Sippin’ and Shippin’. I’m your host, Brian Weinstein. We’ll be kicking in here every other Friday quenching your thirst for an insider’s take to enhance your customer experience. So grab your drink of choice, kick back, it’s Sipping and Shipping time.

All right, welcome everybody to another episode of Sippin’ and Shippin’. I am your host Brian Weinstein, as I am week to week or every other week with my special co-host Caitlin Postel.

Caitlin Postel: Yes, special, I’ll take it. Hey Brian, how are you?

Brian Weinstein: How are you?

Caitlin Postel: Oh, I’m doing well. Getting into the summer, feeling good.

Brian Weinstein: I can’t believe we’re in the summer and I also can’t believe that I saw the next two weeks it’s supposed to rain every day.

Caitlin Postel: No, bummer. No worries. Just more reason for folks to tune in every other Friday. If it’s raining, might as well sit down, sip, ship, listen to some great content.

Brian Weinstein: Exactly right, exactly right. So we are going to recap and so this is a special episode, right? This is episode number 42, and 42, as I was telling Caitlin earlier, this is a number that’s special to me. Right? I’m a huge baseball fan and this was Jackie Robinson’s number and nothing could represent disruption more than what Jackie Robinson brought to baseball and really to the progress of our country overall. So this is a cool episode to do that.

Caitlin Postel: I can always count on you for a good baseball reference, but yes, the 42 Jackie Robinson disruption, which has been a huge buzzword in our industry. I feel like not even just this year, but since e-commerce really exploded disruption, right?

Brian Weinstein: 100%, and it’s a lot of fun watching what’s going on. And I think part of the reason that you and I set out to create this podcast to begin with was because we wanted to get the voices of these subject matter experts who are really revolutionary in e-commerce, right? They’re really changing the game, what it was. I mean, look, it existed 15, 20 years ago, but not like it is today, and like it is today is world’s different than it was two months ago.

Caitlin Postel: Yeah, I think same as the thing of the past, younger generations are craving, wanting, desiring new things, effective ways, and not to mention there’s a lid for every pot out there. Right? So I feel like now with the TikTok phenomenon, just people coming out of the woodwork, you never thought that you’d have similar interests, but more importantly similar thinkers and folks that are thinking outside of what is typically just status quo, which is really exciting.

Brian Weinstein: Okay, but I remember back to early on in season one, we had Habib Salo from Young Nails on, and what resonated with me, and this is really around the conversation of disruption and just changing the game, was that they were never afraid to try something in their marketing efforts and whatever it was that was going to resonate with their audience. He’s like, let’s just throw it at the wall and see what sticks, and I like that.

Caitlin Postel: Yeah, I think it also speaks to something that we heard at our most recent leadership summit where one of our customers was on a panel and just looking to us to be an industry leader and a thought leader and said, don’t wait for it to be perfect. Show it to us when it’s good. It doesn’t have to be great, but it doesn’t have to be perfect because if you wait for perfection, it’ll never get done, right? At some point it’s like starting a podcast, right? You can’t practice to be a podcaster, you just got to show up and get to it.

Brian Weinstein: Exactly. Exactly. And right now it’s become such a volatile world, and I don’t even mean that in a way that’s threatening volatility. It’s just the way things are changing so quickly, so dramatically. Obviously COVID was a huge change, then all of a sudden you have economic headwinds that weren’t there. You’ve got companies that are strapped with inventory and looking to liquidate and then trying to figure out what’s next. And then brick and mortar, it was the brink of death and then all of a sudden came roaring back and now you’ve got all these e-commerce companies who were like, there’s no way I’m going to sell my product in brick and mortar. And now they’re selling their product in brick and mortar and there’s just so much changes going on that to your point, put it out there when it’s good. Don’t wait for it to be perfect because if you do, you’re going to miss opportunities.

Producer Tanya: I mean, there’s always going to be disruptions, but talk about disruptions. You just listed all of them, Brian.

Brian Weinstein: It is it over? Is the episode over?

Caitlin Postel: All right, let’s not get carried away now. When I think of disruption, I think about one of our first season two guests, Jess Owens and Zach Whitaker from Green List. The space of returns is something that we visit often on the pod, but they put a new spin on it as far as peer to peer returns, which typically some folks will think of it as consignment, but they just came with something fresh. Most of the time these inventions come from a story, something that happened. She was shopping online, she wanted that size jacket, they didn’t have it, and she knew in her heart of heart somewhere in the nation, someone had that size medium jacket, size small jacket, whatever the case is. And the second that they sent it back, where does that product go? Why couldn’t she have the opportunity to have it sent directly from that end user to her? Which is an interesting disruptive concept.

Brian Weinstein: We’re having an impact, right? There’s an impact going on with the way that we’re consuming product now, and it does have environmental impacts and this initiative amongst a lot of brands to find some way to be carbon-neutral, to really be more sustainable. And look, we don’t know what’s going to work and what’s not going to work. We have to be out there trying to disrupt and look for ways. And I thought with Jess’s product, and we should probably check back in with her, see how things are going, it’s an interesting concept of the peer-to-peer. And it’s just another way to help reduce the impacts, the negative impacts that we’re having with all this product going here and there. Right?

There’s just so much of it. When you think about … and this probably, Tanya, you could write this down as a future episode, but how are we getting away from, I have bags of clothes that I’m donating, but I know that not all those bags are going to make it to people and they’re going to be tossed? What kind of impact does that have? How are we getting out in front of that? Because I mean, this has only been going on for 100 years or so and the population is booming and we’re consuming more and more. We have to look to be disruptive in those areas.

Caitlin Postel: For sure. And yeah, we really should check back in with Jess and see how that went. Maybe we could link her up with Maya Benson, a rockstar in the venture capitalist space. She was a great episode, love to hear her insight. I think we recorded with her the day that the Silicon Valley bank just went under, which she didn’t seem distracted, but she brought some of that energy.

Brian Weinstein: Yeah, yeah. Fortunately, I think we skated and made it across some thin ice there with the bank collapse and hopefully that’s the end of it. I know there was a couple of others, but hopefully they’re out in front of that and we don’t have any issues. And it was a very stressful time for a lot of smaller companies that had their money there. Maya’s bringing great insight into the industry and she’s investing in some tremendous brands to really see what’s out there. But she did talk about how just with everything going on in the economy, money was sitting on the sidelines right now and there was great companies out there still looking for funding. But until everybody had a clearer picture of where the economy was heading, no one was really going to be rushing in to make those investments as of yet.

Caitlin Postel: Right, and then if you take the approach of like, let’s go glass half full, yes, the money’s on the sideline, but now this is driving some really disruptive behavior. Only the best of the best are floating to the top and getting that funding and being able to get invested. So just bringing a higher quality I think is how she expressed it of founders and entrepreneurs because those barriers are so high just driving that overall disruption.

Brian Weinstein: Yeah, absolutely. And what I love about Maya too is I think her and her organization spend a lot of time investing in female founded businesses, which is great, well deserved and well needed space that needed to be recognized. And then somewhere right after that, I think it was right … no, maybe it was right before, I got hijacked. I got kicked off the podcast for an episode.

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Caitlin Postel: You did, you did. That’s right. And when you said it, I felt like, oh, my goodness, hijacked, it sounds so bad, but come on. It was great, Woman’s History Month. We had our very own Eva DeCheco, we had Ella Monarch and we had Bree Chapman on, which I really loved leading that discussion with those ladies, really admire and respect them and just their bosses and they do their thing. And I loved when Eva just spoke to the fact of having a seat at the table just in general, whether that’s children all the way through female leaders and everyone in between. How do we create that equity and really just use our voice to drive change? I thought that was really cool to hear it from one of our internal leaders.

Brian Weinstein: It’s interesting because when I first entered the workforce, there was definitely more chauvinism that was there, but it was interesting. So when we had Joanne Marciano, who’s one of my favorite people to work with on the episode, and we’re around the same age, she said that she had a great experience when she entered. She felt like the men that she was at the table with gave her and allowed her to have her voice, which was interesting because you didn’t always see that early on in our careers. And I remember feeling somewhat uncomfortable in some rooms because I didn’t feel like there was enough voice given to the female leaders. So that was great to hear that she had that experience and that she had good female leadership as mentors, but also that she found some mentors in some of the men that she worked with that helped give rise to her. And speaking of a boss, total boss lady right there.

Caitlin Postel: Yeah, and it was interesting that that was her experience across all segments within this business because I think she started at Old Navy, hopped around and then what? Well, she first started in retail and then going to Old Navy and then eventually graduating up to I think … What is she now, Brian, the COO of Grace and Clovier? So I think it’s a good point to see that that was her experience across all of those channels, which is great.

Brian Weinstein: Is it Clovier and and not Postel?

Caitlin Postel: Okay, I knew that’s where it was going. All right. Yes, it’s clothe air. Caitlin Postal stops there.

Brian Weinstein: I just want to make sure.

Caitlin Postel: It’s my next stop after Target. Loop it all together.

Brian Weinstein: If we’re going to frenchify everything, that’s fine. I’m okay with that.

Caitlin Postel: Let’s get it. Oui, oui.

Brian Weinstein: Why do we all talk with these accents?

Caitlin Postel: We don’t. We don’t.

Brian Weinstein: We don’t. We don’t.

Caitlin Postel: But it is Clovier.

Brian Weinstein: Exactly. Exactly.

Caitlin Postel: So we wrapped up season two in women’s month with Julia Perez who is I think we said fashionista turned CMO of Owen. She brought up an interesting point of just how brands are communicating to end users and the use SMS, especially during and post COVID. SMS, brands that you love and admire sending you text messages. I never thought I would see it. Sometimes I love it, sometimes I don’t, but it’s been effective for sure. It definitely drives me when I see a text message come through. If it’s something that piques my interest, I’m heading right to that website to see what’s hot and new, what’s trending as I usually am, just to be ahead of the curve.

Brian Weinstein: And being ahead of the curve and understanding and changing and evolving and using different marketing messages. We had ar Arthur Fit on from Reed Jewelers who talked about when he was at Avon, right? A business that was basically selling door to door. It was having the parties, it was that type of business and transforming that business into a much more online present business where you could go on and place your orders, yet not having conflict with your boots on the ground salespeople who are still selling within their communities and how you can transform that whole digital aspect of a legacy company and make it something that’s more relevant to the market in e-commerce. I thought that was a great episode and I thought it was a great the way you have Arthur who’s talking about some of these more legacy businesses versus Julia who’s really talking more about these digitally native, newer companies and how they’re transforming their marketing.

Caitlin Postel: For sure, yeah. Arthur gave a lot of great insights, some gems, his 90-day plan. And for someone to be an information and chief technology officer, I liked how he brought it back to people, which is interesting and I think it’s something that we realize within the business too. As much as you can automate in robots and chat GPT, people are the main drivers. He talked about mentorship, which is something that came up a ton between season two and season three, the power of the mentor and the importance as a leader and a coach to understand each of the folks that you’re working with, their capabilities, their strengths, and how you can use that to drive overall success within an organization.

Brian Weinstein: Yeah, yeah, absolutely. And really building an organization where you’re eventually going to be replaced, right, which is a good thing. I mean that was his ultimate goal was find the right team, structure and person to replace him.

Caitlin Postel: Yeah. The power of the succession plan. You know it, the person knows it, the team knows it. Let’s get it. We got to move forward. Of course there’s success at this time, but who are you going to pass the baton to?

Brian Weinstein: Exactly.

Caitlin Postel: Pun intended with the baton reference, big R.

Brian Weinstein: Nice. There you go, big R. There you go. R World, look it up.

Caitlin Postel: Speaking of the big R, I picture your alma mater, the big R, the Rutgers, right? Then I also picture a varsity jacket, right? When you get that big letter moving from JV to varsity, something that we’ve talked about a ton. I think even from back in season one, we had Chelsea Jones from Chelsea and Rachel Co., and her tips and tricks of being able to elevate and bringing the business to the next level of whether that’s a facelift from the site, optimizing your tech stack, using post-purchase SMS, whatever the case is going from what we call emerging into enterprise, JV to varsity, let’s go.

Brian Weinstein: So their organization focuses on really the center of the e-com ecosystem, which is Shopify or seemingly Shopify and steering brands, but also making sure that those brands understand that sometimes less is more, and that’s better and to really navigate their company.

Caitlin Postel: Yeah, keeping things simple, less is more, using technology to meet customers where they are, communicate to them how they want to be communicated to, and most importantly, just adaptability. How can you stay nimble as you grow? I think some folks fear that they lose some of that nimbleness going from startup as the business scales, but being able to leverage some of those tips and tricks I think was a key takeaway in that episode.

Brian Weinstein: Yeah, and again, this going back to adaptability, adaptability being disruptive, understanding that what’s effective right now may not be effective by Friday, right? And you just have to continue to try.

Caitlin Postel: Right. Talk about, in that case, Brian Tigner, Thirty-One Gifts, right? You might think that he’s touched a ton on … the whole conversation was about customization, personalization. You start out as a founder, you’re writing notes, handwriting notes. Okay, that’s cool when you’re doing 50 orders a week, now you’re doing 500, now you’re doing 5,000. You better find someone that has very identical handwriting to you, or you better find a solution that’s going to be able to keep giving that experience or maybe pivot from that experience.

Brian Weinstein: Yeah, it’s interesting. We’ve had some opportunities along the way I think, to your point, around handwriting notes, and it’s great and I understand that everyone wants to find a way to resonate with their audience. They want to be able to have these loyal customers with certain expectations. But as you begin to scale your company, if you want to scale your brand, if you want to reach a broader audience or even just extend the audience beyond what you currently have, but maybe with that same type of interest group, you have to think through what is going to work, what is scalable and what’s not. Brian Tigner, I think did a great job of talking about personalization, setting expectations, maybe limiting the scope of what you’re giving while you’re still giving value to the customer, whether it’s embroidery, embellishments of some kind, embossing, engraving, anything like that. But what can you do that can extend beyond your audience? So if you go 2X, 3X, 10X, that you can still produce and reach and exceed your customer’s expectations.

Caitlin Postel: Right, and can’t be everything to everyone, but planning for today, but really thinking forward, what does that look like a year, two years out? Even just something as simple as monogramming just really exploded. How do you do that? How do you now be able to have that throughput? You always say it, you’ve said it since the beginning, it’s math. The numbers are the numbers. Whether you have 5,000 orders or 50 orders, this amount that can go through that process is the same. So how do you make sure that you can really maximize that or think outside of the box or maybe be a little disruptive is saying, how can I partner with a true expert to be able to execute and have your vision come to life? Which is always cool to see.

Brian Weinstein: Yeah. Yeah, exactly. I mean, look, we all have our areas of expertise and relying on the experts is what’s going to help you continue to scale in your growth trajectory. Or if you partner with the wrong people, and regardless of the service, it could be a software, it could be a 3PL, it could be anything, a manufacturer, if you partner with the wrong people, it will only hinder your ability to scale.

Caitlin Postel: Right.

Brian Weinstein: And the most successful, I think of the brands that we have seen are ones that have made sure they’ve aligned with the right partners and put themselves in the best positions moving forward. And then, of course, there’s a little bit of luck involved with all of that, but that’s what’s going to give you the best odds to continue to grow your business.

Caitlin Postel: Yeah. Speaking of appropriately partnering and leveling up, we had Terry and Rob, our very own automation team on talking about the use of automation and doing it strategically and not just jumping on the bandwagon. Right? A lot of ROI discussion, a lot of pairing together people with technology, not just, you get a robot, you get a robot. We all love chat GPT, but how are you using it effectively and what’s the power of people that are driving technology? I really like that conversation of ABC, 123s of automation.

Brian Weinstein: Yeah, exactly. And look, automation is not for everybody, might not be for you right now. There are always repeatable tasks where you might be able to replace them with some relatively inexpensive piece of automation, let it be an auto bagger or something along those lines. Don’t go out there and just think, to your point, Caitlin, then you get a robot and you get a robot. It just doesn’t work that way and it may not be the right fit for you. So be smart about how you move it forward and what you’re investing your dollars in.

Caitlin Postel: Yeah, you hit the nail on the head with the money, right? It’s so sensitive right now. Folks are thinking twice about spend, but if it does make sense and the ROI is there and you think that this is a business that’s not going to change too much. And I think that was the overarching thing too, right? Automation is cool, but now how can you pair automations together as business evolves? And I forget what his quote was. I can’t think of it off the top of my head, but just basically that not consistency is the enemy of automation because then-

Brian Weinstein: Yeah, that was a great quote and I don’t remember what it was either.

Caitlin Postel: I’m surprised. I was leaning on you for that one.

Brian Weinstein: I know, and I’m trying to-

Caitlin Postel: Tanya, help us. Do you know?

Brian Weinstein: Okay, so we talked about the economics of all of this. Any predictions about what the future holds here?

Caitlin Postel: Oh, man, it’s hard to say. I mean, we’re halfway through ’23. Is the shallowness coming? Is the mark coming up? I don’t know. I feel like we’re starting to see some movement, but I’m not too sure. Brian, what do you think?

Brian Weinstein: There’s definitely mixed signals. Business is a little bit softer just in the sales space of what we’re seeing our brands do, people are diversifying. So I think it’s, again, everyone’s trying to be innovative within their own world, and I do believe that will propel people and get people set up for success coming out of it. So they’re exploring different channels, they’re exploring different marketing efforts. The consumers are still there. There have been some layoffs, but I don’t know that the economy right now is in terrible shape. I mean, I still feel like the unemployment is relatively low and I see people starting to gear up for ’24, which is a good sign. I do think we still have to work through some inventory that our customers I know are trying to liquidate and go in that direction. So I feel like what I’m seeing are people making the right moves for six to eight months from now.

Caitlin Postel: Yeah, I think it’s important now to leverage these relationships and partnerships and being able to work closely and collaborate to make sure that everything is going as planned, but more importantly, when everything does pop, that you’re well positioned to be able to utilize and really leverage existing partnerships, because we all know that moving is super expensive and making a lot of changes during this time. I don’t think the wallet warrants it and just to be able to solidify that where you are is the right place to be. Or maybe it’s time to jump ship in six, eight months. I don’t know. I think this upcoming peak season is going to be very pivotal and very … it’s going to make people think one way or another.

Brian Weinstein: Yeah. I do believe it’s going to be telling where people are spending the money because they still believe there’s money out there and you can only scream recession so many times before people say, maybe I should stop spending as much. But will they turn towards travel and leisure? Will they turn towards buying product? What’s going to be the prevailing attitude as we start to feel like, okay, maybe we’ve hit bottom and we’re starting to come back up?

Caitlin Postel: Fair enough. I wish that I had a Jackie Robinson reference to pull this together, Brian, but I’ll leave that to you. On the spot, go.

Brian Weinstein: On the spot. So are we going to steal home?

Caitlin Postel: Oh, well, you have to because the budget doesn’t allow you to just buy it.

Brian Weinstein: Exactly right. Exactly right. No, you know what? And again, the podcast overall for me has been extremely rewarding. Having all these great guests on that are really these subject matter experts that are opening my eyes to certain aspects of the business that I really did not have any expertise in, did not really have any knowledge in, has been great. And we’re looking forward to a long list of guests, but it’s been a lot of fun.

Caitlin Postel: Yeah. So brands, as you’re facing outside parameters, the uncontrollable, Jackie Robinson, let your talent shine, stick to the course fundamentals, it’ll turn, it’ll turn.

Brian Weinstein: Exactly right.

Caitlin Postel: If all that fails, just steal home.

Brian Weinstein: Just steal home. Just steal home. You want to walk us out?

Caitlin Postel: Sure. Thank you, Brian. Thank you, Jackie Robinson. Thank you, producer Tanya. Thank you all for listening. Make sure you tune in every other Friday on your favorite podcast platform or at Thank you, everybody.

Brian Weinstein: Peace.

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