Mastering the Art of Failing
Mastering the Art of Failing Podcast
From Rocker to Entrepreneur: Phillip Jackson's Journey in the World of E-commerce

From Rocker to Entrepreneur: Phillip Jackson's Journey in the World of E-commerce

Season One, Episode Six: Former touring rock star turned owner of a highly regarded e-commerce media brand, Phillip Jackson, shares his unique journey.

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Phillip Jackson, the Founder of Future Commerce, has had an unconventional journey in the world of e-commerce. Prior to establishing one of the most respected publications providing insight and research into the world of e-commerce, Jackson aspired to be a rock star.

Yes, you read that right, and no, this is not a tale of a washed-up rocker trying to relive glory days. Jackson and the band were one step away from making it to the lineup at Warped Tour, palled around with the likes of Underoath, and had so many character-building moments that it’s hard to imagine who he was in a past life. That is, of course, besides the remnants, which we’d like to say likely explains his still spiked hair.

Jackson’s story is in part about being unsuccessful as a rock star, but it’s more so a pathway that led him to reshape his creative energy and build a brand that an entire industry looks up to. That pathway shifted as the responsibilities of building a family came into the picture, having to self-learn the concept of brand building and storytelling (thanks MySpace), and ultimately develop an e-commerce media company. He also doubles as an absolutely insane ultra runner who handles the Florida humidity and swamps as only a true rock star can.


  • Resilience is Key: Despite numerous setbacks, Jackson never gave up. His determination to succeed was a driving factor in his career transition and the success of Future Commerce.

  • Transferable Skills: Jackson was able to use his skills from his music career, such as project management and marketing, to transition into the e-commerce industry.

  • Embrace Change: Jackson was open to a career change and embraced the shift into a new industry. This flexibility and adaptability were crucial in his journey.

  • The Power of Networking: Building a strong network can be a significant asset in your professional journey.

  • Balancing Work and Personal Life: Success often requires sacrifices, and finding a balance between work and personal life is crucial.

  • Importance of Mission Statement: Having a personal mission statement can provide clarity and help in decision-making.

Producer’s Note

Mastering the Art of Failing is now recording new episodes after a small break so our lovely host can spend time with her new little one. If you have recommendations for future guests, please send them our way. Until then, we will have sporadic publishing schedules.

Transition to E-commerce

Jackson's journey started as a musician who dropped out of college to tour with his band in the hopes of becoming a rock star.

With the harsh realities of the music industry, Jackson found himself in debt and in need of a career change. He realized his skills in marketing, design, and project management could translate into the booming industry of e-commerce.

The Power of Networking

One of the significant factors in Jackson's career progression was his networking skills. He mentioned, "A lot of my network was built in the professional career and was not durable enough to last for decades, which is something I look at very jealously of people that do have a college network that continues to help deliver value for them in the future."

The Birth of Future Commerce

Jackson's resilience and determination led him to found Future Commerce, a media brand that covers the intersection of culture and commerce. Drawing from his past experiences and skills, he was able to transform his life and career, creating a successful media company.

As Jackson's story shows, the path to success is often winding and full of unexpected turns. However, with resilience, adaptability, and a willingness to learn and grow, even the most daunting challenges can be overcome.

Balancing Work and Personal Life

Jackson also shared the sacrifices he made along his journey. Balancing his demanding career with his personal life was a challenge. "I had to be away from my family for 23, 24 weeks a year. And we had young kids. You know, my kids are 11 and 12 now, and they went years and years where dad was on the road," he reflected.

His story is a reminder that success often comes with sacrifices and that balancing professional aspirations with personal responsibilities is a challenge many entrepreneurs face.

Importance of Mission Statement

Jackson attributes his clarity of purpose and decision-making ability to having a personal mission statement. "I feel like I've had fewer opportunities to look at something as a true failure since I decided to adopt a mission statement for my life," he said.

This approach can help entrepreneurs stay focused on their goals and make decisions that align with their core values and mission.

Phillip Jackson's journey from a rock band member to a successful e-commerce entrepreneur is a testament to the power of resilience, adaptability, and continuous learning. His story serves as an inspiration for anyone looking to reinvent themselves or navigate the challenging world of entrepreneurship.


Mastering Failing uses automated tools to create a transcript of our show. Please excuse any typos and hallucinations that we’ve come to love from our new AI overlords.

Phillip Jackson: Hi, I'm Philip Jackson, and 20 years ago, I dropped out of college to go on the road with my band and to become a rock star, and it all fell apart. Today, I am the founder of Future Commerce. We are covering, as a media company, the intersection of culture and commerce, and I wouldn't have done it any differently.

Alex Love: uh, musician, and that was always something that I wanted to carry with me in life. So let's talk about it. What kind of band, what did you play, sing, do, and, and what led you to the decision that, you know, this is it. I'm gonna make it.

Phillip Jackson: Uh, well, yeah, I, I think the, well, the decision seemed to be really clear when the opportunity came. It was like anybody who was in a rock band. I was in a rock band and I'd met a bunch of guys and this phenomenal vocalist, a woman named Jackie and who later became my wife. We had this cool little jam band that we had formed we all met at church in our youth group and we were in the youth group band.

And, but, you know, we got to playing and we were, I thought we were really good and we had some friends of ours who had run a recording studio and they wanted to give us free recording time and that was a big deal back then. It was, like, really expensive to record stuff. Now, you know, Billie Eilish does stuff in her bedroom, but that wasn't how it worked back then.

And we produced an EP. And a bunch of friends of ours started shopping it around and then we started getting offers to go play. And then I had someone say, come come spend the summer and tour around with us and be the opening act. And then, you know, acts that you would know today were friends of ours who were doing this too.

So I had so much peer pressure at the time that it just seemed obvious that the next step in my life, there's this cloud that parted that gave me this opportunity of go on the road for a summer. And go tour warp tour was in was in Seattle and playing in like Bremerton, Washington in 1999.

And I was like, I'm just going to go. I'm just going to go do it. And we'll see what happens. And from 1999 to 2005, I tried to make a full time living as a musician with only two years of college under my belt and thought, I can always go back, but that's not exactly how it panned out. A lot of, there was some ups, but a lot of downs years and years and years of, of struggle actually, and

Elliot: All right, hold on. I gotta interrupt Alex because I know you got some questions here. Can you clarify, did you play at Warped Tour? Is

Alex Love: Yeah, I was, I was gonna ask that. Did you play Warped Door?

Phillip Jackson: I played on the, on the show that plays right before Warped Tour, trying to get into the stage as like an auxiliary act. I didn't get onto Warped Tour. I had a friend who snuck in and made headlines and they conned their way into playing Warped Tour.

Elliot: That's amazing.

Phillip Jackson: but I, I didn't get, I didn't get on Warped Tour, no.


Elliot: We're like one connection removed away from a Warped Tour

Alex Love: Hey, you're closer than either of us, but R. I. P. Warped Tour, because that was definitely a good time, Team New Jears. But anyway, cool. So let's dig into that. Six years on the road, right? You said there's a lot of ups, a lot of downs. Talk a little bit about that, right? What was the experience like? How did you survive?

What did you learn?

Elliot: I'm

Phillip Jackson: a lot. Unlike, you know, gas station, like rolled tacos. You know, I we had a not small affair. It started with four guys in a van. But by the end you know, we kept building the stage act. And so we had a 32 foot trailer that we would pull around. We had like multiple trucks and vans and and lots of equipment.

Yeah. Yeah. That we, we carded around. I think at the, at the end, we had 15 people in our total act that was traveling with us. And we it was just never really terribly efficient. It sounds exciting. It's a much better story than it was as a lived experience. It never really got off the ground.

And I think that that's, you know, we had no, we had none of the, the. Efficiency of distribution in the internet age. We were like pre my space. So everything that you ever wanted to do, you had to try to like book by cold calling venues and you had to have a friend who like knew somebody or knew a producer or knew, you know, a booking agent.

And, and it was all by word of mouth and all by who you knew. And unfortunately, fortunately, and unfortunately, all of our friends who had connects, We're also trying to do that for themselves. And so you're in co opetition. And I see this a lot in business now. Like we are partnered with other bands who are making it really big.

But at some point they get to a gravitational pool where they have an escape velocity. They, they go on to actually play Warped Tour. So some friends of ours at the time were like, the guys in Copeland or the guys in Anne Berlin. I grew up playing clubs, you know, with the guys that went on to become Under Oath.

I, I, I opened for a band that went on to become, called Earth Suit, which is now Mute Math who played the last 21 Pilots Tour. These are Grammy award winning artists and as they started to get more successful you're trying to replicate that success through the things that they were doing, but you have none of the actual monetary success that comes along with it.

So what wound up happening every year is we should go deeper into debt trying to make ends meet And then, you know, technology comes alongside to maybe that's a way I can make money. I can build websites on the side for people. I'm doing it for my band. Why wouldn't I be able to do it for, you know, the local credit union who needs a website?

And that's actually how I got into technology. It was first as a as a marketer for my band, but also then, you know, the next stage is like, how can I take that skill and just try to like, put gas in my van to get to the next gig with that skill. And try to make some scratch on the side.

But yeah,

Alex Love: So talk about that transition pivot point, right? How long into being on the road, one, did it get tiring, right? You're not seeing the monetary success. You're seeing all of your friends, you know, grow up, do bigger things, play Warped Tour XYZ. When did you start to think maybe I do need an exit plan?

Maybe this is not you know, my end goal in life.

Phillip Jackson: every other month for, for five, six years, I you know, I, I think things really changed when Jackie and I got married. You know, we were we fell in love in, in, in a Midwest tour we were doing. We happen to be, she came and sang with us at a gig in Janesville, Wisconsin, Janesville, Wisconsin.

I think that's right. We played a, a, a small venue in Janesville in 2003. And it was. Valentine's Day, and we were both, I think we were couch surfing. We were like, we couldn't afford to stay in hotels. We were like, staying in people's homes. And we went on a date to Walmart. That was our date to Walmart.

And I had, I didn't have any money. I had no money. I couldn't hardly buy her anything. I think I put a I bought her the Elvis Presley reissue CD for Valentine's Day on a credit card, and I think that was like a pivotal moment for me of if this relationship is going somewhere and we're really going to do this, what is the plan?

Like I have no life. Music has been the life and it's easy to assert. You know, couch surf when you're a single guy as a musician what is the next stage here? What am I supposed to be doing? And I feel like even after we got married, we both started asking ourselves, like, how realistically, how much longer can we do this?

It's very hard to be married. I think to begin with very hard to be newlyweds, very, very hard to be newlyweds, you know, in the van with seven guys. So we, we I think that was the turning point for us, but I think crushing debt also made it a had to, something had to give eventually.

I think by the end of it, we found ourselves in almost 50, 000 of credit card debt. And, you know, I'm 25 at that point. And and I have no income. And I don't have a career. And I, I think we, we just came to terms in November, 2005. And we're like, I think this is it. I, we, there was no choice. I think we just had to come down to it.

Like all, all hope had been lost at that point. It was the holidays. We're going to go home for the holidays anywhere. Cause we're on the, on the road 11 months a year. It's I just don't think we're going to go back out for the next. And that was it. Yeah.

Alex Love: Said you did college for a little bit. Did you have a career path or progression? What were you studying in college? Did you have a plan?

Phillip Jackson: Yeah. That's its own story too is, you know, I had a, a, a really strong desire to You know, try to be in theological studies and specifically to enter into some form of ministry. I really early on to that was another part and an advantage that we had in the musical act is you had all these crossover Christian bands that were all, you know, making a big at the time and had this net, like a network of places that you could go play.

Churches would put on events. You'd have big tours that were making it at the time that were, yeah. You know, faith based tours and a lot of folks always want some sort of like form of entertainment for big charity outreach stuff. You know, I had an amazed some of the greatest stories of my life are from, you know, missions based events that we would go play music at, you know, the North slip of Alaska and point hope and like spending a month, you know, with native tribes and going out on like ice shelves and going seal hunting.

Like it's crazy stuff, but it was all under the guise of we were a supporting act of a larger outreach piece. But I, I also realized Alex real quick within a year of being in seminary that I was like, maybe this isn't for me either. And I, I feel like the opportunity to, to, have some approximation of the feeling of doing that work sooner than what the, the training and the schooling allowed was also like an excuse for me to run away from it. Because I don't know from a career path perspective that that's really what I wanted. I wanted something bigger. I wanted to stand on a stage to be honest with you.

But I wanted the stage to be bigger than I think what a church could have afforded. And looking back now I don't know that I could have said that out loud back then, you know,

Alex Love: yeah, yeah. Sounds like you've lived a couple of different iterations of your life up to 25, which is still so young. You know, you didn't necessarily have a career to go back to or plan to go back to. You said you started picking up a lot of these marketing pieces for your band specifically. So how do you start to pivot that into the career that you have today?

Phillip Jackson: Well, you know, let's, let's think about the era in which that happened. So 2005 was the beginning of social media. So we had my space was in its early stages back then. And as a, you know, when you're in a band you do a lot of things that. You gain a lot of skills especially when you're bootstrapping and you're like selling CDs out of your car.

You gain a lot of skills to have to project manage large efforts all the way to completion. So you actually gain the skill of creating campaigns, drawing awareness. Learning how to package things in ways that people want, learning how to reuse and repurpose existing creative so that you don't have to reinvent the wheel all the time.

You have to tell your story over and over and over again to a new audience who's never heard of you and doesn't care about you. And you have to get really good at that. We found, you know, we would we also found every time we put out something new, that was the thing that always hit and it had its own little half life.

If you put out something new. And this is before Spotify, right? You, you had to put out like a physical piece of media, but if you put out something new it was a form, it was like a revenue stream for a limited amount of time until people were bored of that. And you know, the game had always come down to, it's the same skillset that a modern marketer uses in like a CPG business or an apparel business, any e commerce centric business is it's the same set of skills.

So whether it was us producing tour posters or, you know, postcards to support. You know, and tell people about the newest EP or CD that we were putting out. I realized as I was getting these side hustles, these gigs to create websites for people that were e commerce websites I realized, wow, this is all the same stuff.

My print background in Photoshop has a direct line to imagery on the web. I was the only person who could make marketing graphics because I knew how to work Photoshop. It really like the path in was really just I took whatever job I could get first and that job I'm so thankful for now just happened to be a startup that was building e commerce websites in the B2B space specifically for direct mail and direct marketers who were trying to reach customers through through mail advertising and I learned so much in those first couple of years at that company Where I thought it was going to feel like I was settling and I thought it was going to feel like a failure.

I had to pivot in my career. Now, that feeling of feeling like I was behind has stuck with me for 20 years. Because I was, you know, ostensibly 6 plus years behind career wise from anybody else. But I had that dog in me if you will. I had some fight that I didn't want I didn't want to be perceived as being behind.

And so I worked harder probably than any of my peers at the time.

Elliot: Honestly, I think I'm What we're getting to is imposter syndrome to an extent, it's healthy to an extent as long as you don't like, let it drag you down, but having seen your work, the things that you produce, the brand behind you, it's very clear that that hunger has allowed you to develop something that has become a necessity and You know, essentially a research arm for a lot of folks in the e commerce space.

I can definitely attest to that, you know, maybe you didn't go and get a four year degree, but the things that you put your hands into to build that necessity, you can't get necessarily that kind of hands on experience. with a fancy piece of paper. And I can say that from experience because I have two of those.

What you learn and what you take away from those kinds of situations are entirely different when you're living in it. And you're, you know, you're scrapping by to get more taquitos over at 7 Eleven while you're on tour. I, I totally get that. I think being able to understand that aspect is what allows you to really excel.

Either you, you know, you drown or you. Yes, sink or swim. So I applaud that. I think that's fantastic.

Phillip Jackson: Thank you. I, I will say the, and this is, this is the thing that I remind myself every day is nothing really has you know, to get into the more of the, the modern era is now that I'm an entrepreneur and I have a team with me, it feels like the old days to where I have this I have this road crew and we're because I have seen the worst of the worst and I've done things that, you know, felt so horrible.

Nothing scares me anymore. Dreaming big is not really all that difficult for me because I'm using every skill that I've ever gained, you know, from production design, event management you know, working with, you know, unions to set up, you know, getting certificate of insurance, just to like load into a building, you know, having fire marshals try to shut you down.

I've been through all of it. And very few people in in our space have that kind of experience already. And I'm drawing on that experience now. So what really I, you know, I'm really actually so grateful for that time. But, it really felt like a, a weird detour and a side quest, very much the side quest and not the main quest for 16 years and until we get to present day which now it all feels very purposeful but it certainly didn't feel that way.

Elliot: Well, the other aspect is a lot of what I think you've told your background story, the things that you've done, you've never. Maybe you temporarily paused them, but you haven't severed them. You know, this is for the record, anyone listening, this is the first like face to face conversation I've actually had with Philip.

We have bonded over terrible things like he will run in the Florida swamps. We are both ultra runners. He does much horrible, more horrible and crazy things compared to me, but yeah, I, Yeah, no, I think being able to understand like your background and seeing the story that you've run through, they're still there.

I definitely see you still doing production work for you know, different organizations that you're a part of. Obviously they don't pay the bills, but you're able to use the things that you have crafted your own business, the revenue from that to be able to still spread joy through the things that you love.

And I totally get that. I think that's fantastic to be able to do that. Now you have money and you're able to, you know, take care of your family.

Phillip Jackson: makes it so much easier to be honest with you is you know, also now having a, what is a very creative team around me. You know, the, the, the goal today is can we, you know, again, as a media company, we, we have podcasts, we have newsletters. It's not all we do. We take this idea of like creative creative aspiration and we infuse it into everything we do because we believe the, you know, the modern marketer, brand marketer e commerce operator deserves.

The same kind of beauty and the same sort of inspiration that they deliver to their customers every day. And for some reason, in the business to business space, we. You know, we have relied more on the journalistic and trade industry approach to delivering information. And I think that's where I have the skill set and and now this earned audience in that ecosystem to, you know, create and attract more creative folks around me to.

support that mission. And that's where everything you hear from future commerce is, is created of our own accord. Like we create our own audio branding. It's all my musician friends and myself for who have now we're all grown up and we all, you know, we all want to use our, our, these giftings and talents in different ways.

We're creating all of this music from scratch. I now get to work with my heroes. Not to get too deep into the right now, but I was like, something I never ever thought would ever be possible happened this last year back in February I had struck up a friendship with the former creative director of the Smashing Pumpkins, which is like my favorite band and I would have killed to have talked to anyone from from that group You know, 15, 20 years ago, and they never would have given me the time of day.

But now I'm at a place in my life where people in that ecosystem, especially in entertainment are needing more business centric creative development work, and I am all too happy to give them the opportunity and the platform to do it. And people look to future commerce as the only ones brave enough in our ecosystem to put someone like a Linda strawberry as a creative director who's worked with Kat Von D and Lizzo and the smashing pumpkins and Maxwell.

And, you know, To take her, her creative aesthetic and apply it to the world of B2B, I don't think anybody would ever go reaching for it. I'm only bringing the things that are inspiring to me, to the audiences, looking for me for inspiration. And that's like the raddest thing on planet Earth. Gets me so excited because what a cool thing.

You know, what a joy.

Elliot: I'm

Alex Love: first off, that's amazing. The last concert that I went to was actually the Smashing Pumpkins, so that's super cool. And we didn't bring this up in the beginning, but I'm actually seven and a half months pregnant, so we, my husband and I love music. We've taken our daughter to eight or nine concerts at this point, trying to get her of a wide variety.

But my heart is in the 90s grunge area, so hopefully you enjoyed the Smashing Pumpkins. well, you've definitely seen Linda's tour visuals. That's her, you know, all of the aesthetic from their work of the last 10 11 years from Shining Oh So Bright onward has been her incredible incredible creative talent.

Yeah, so cool. Very, very jealous. So let's talk a little bit about the pivot point though from, you know, we left your story where you took a role, you were learning a lot in e commerce space and direct mail, but like you decided to start your own company, right? Walk us through that decision and how you got there.

And any of the lessons learned you brought forward

Phillip Jackson: Well, there's, you know, I, I think the conceit of this, of this property is to talk about failure. And I, I think that it has really not been a, it's been a nonlinear line, even from the, the early days of having this great opportunity in a growth industry, which, you know, again, so lucky and so fortunate.

How many people get to work in an industry that's been up and to the right for 20 years that, you know, it's a, it's an incredible thing. And you know, I could tell you about the time that in 2009, I just happened to start using a software that became. You know, the global sensation for e commerce at the time and that was luck, but it was that same software also that I wound up, you know, creating some of my greatest failures.

I, I, you know, introduced security problems to certain clients. I've, I accidentally dropped production databases live, you know, during a gigantic accident. You know, appearance on the today show I've done some crazy stupid stuff to you know, bigger stages, but you have the stakes are higher to write one thing I've been very fortunate with is that.

At least for the past, I'd say 10, 11 years, I have worked for employers who always give me the opportunity to pursue outside passions and to do it publicly. And that's where this, the business and this entrepreneurship journey really comes from is that I was able to establish trust that I was Yeah, I was a team player and I was helping to build the team and helping to build the brand of the company that I was working with and one company in particular, something digital had owners that saw the value in my public participation in a software ecosystem is being someone that was notable and a public contributor and they let me run with that and they let me operate a media brand that was separate and apart to what they were doing, just believing and trusting that there was a halo effect.

Something we talk about a lot presently on future commerce is this idea that it's just getting more expensive to live in the modern world.

And rather than do without a profoundly modern thing is that people have multiple streams of income so that they can live the life that they want to live. You can do that. I think over employment is its own. He's like almost a million subscribers on the over employed subreddit at the moment. People are like maximizing their life to max min max for income.

I call this the need trippin or. It's not that you want to be a, want an entrepreneur. You've probably heard of a entrepreneur. A entrepreneur is we all have to have a multi, like a second or third stream of income depending on where you live. You might need, you know, a third stream of income just to live an upper middle class life.

And I needed the second stream of income. You know, we had two kids and and I, you know, I've always had some sort of like consulting gig going. I just happened to start a podcast that took off. And I was in the right place at the right time. And I started a podcast that grew overnight to have 100, 000 listeners back in 2000 and 14.

And. It was one of it, you know, it was the only media property of its kind serving and underserved audience in a niche software ecosystem that was in a growth industry that was spending lots of money on advertising. I just happened to be in a great place where this thing took off and I had the freedom and this is the other thing that you, you can engineer.

I had the freedom of a full time employer who said, go do that because it's helping us. And we're not going to mess with it. That's all of those things. I think are rare. And they're profoundly just wonderful strokes of luck. But that that's really, I think the pivot point in the, in the current era is well, how far can I take that?

And it becomes a challenge to myself. I like doing hard things. How far can I take that? Can I grow that into more than one podcast property? Today we operate six. Can I grow that into more than one you know, more than just podcasts? Can we do written content too? And today we have three newsletters and you know, can we do video?

And that's the thing that we're trying to solve for right now that we've not done very well. Can we do physical events? You know, I have a thousand people RSVP'd to come to my Art Basel event in two weeks time. And, you know, we sell out our events, people come, you know, from miles away, people are flying in from Germany to come to this Art Basel event just to come to see what Future Commerce is about to do.

And that is like. Kind of mind blowing to me because it really all feels like yeah, it really feels like it's, it's the result of a lot of people's trust in me over a long period of time.

Elliot: Yeah. Again, I, when I was in the e commerce world, I became very familiar with your work and your antics occasionally on social media. So it was really easy to understand that there's a personable, it's true, but like there is a person here. It's not just like a brand trying to build something is a person building a brand when ecosystem and, you know, you don't really see that kind of stuff out there.

And it's not effective a lot of the time for these organizations that try to basically create like these mini influencers, which I apologize if you hate that term, but you're like an e commerce influencer to a, to a degree, but yeah. But I feel like this is a really good opportunity since I haven't really opened this door yet, but can you.

Maybe explain what future commerce specifically does. What is the purpose and the intent? Obviously I am familiar with it, but I feel like it would help maybe open up the doors for people now understand where we are at this pivot point. What have you built? You know, what does it stand for and you know, how does it help people?


Phillip Jackson: Yeah, that's maybe one way to help you understand it because I could explain we're a media company. But it took me six years to figure out that we were a media company. I, I just had a podcast, right? Or I just had a newsletter. And because it was a side hustle, we weren't trying really hard to make it a a business because we were making money and we had full time jobs.

My co founder and I, and we had a small staff that was helping to operate it. It was very much a side project and because we weren't taking money out of it. We could invest in things at a bigger scale than, you know, like we could spend too much money on a print project. It's not going to hurt us. We could spend, you know, a lot of money on something, you know, on building a custom website for a property launch because we didn't have to bootstrap that sort of thing.

It just, We have the funds available to do it. Everything shifts when you want to make this your full time job. And then you have to really try to understand what, what are we about? What are we trying to do and how to successful media companies operate? Because we've never done that before.

I thought we were still in the e commerce business until I came full time to future commerce 14 months ago now. It wasn't until 14 months ago, I realized, Oh, wait, actually my business is media. My audience is the e commerce professional. And there are two different things. And I had to let go of the fact that I'm no longer going to be the expert in the room around things centered around best practices around e commerce.

My, my job is to try to create an environment and a culture and a brand that people who are the experts want to come and be associated with. How do I do that? And the best way to do that is to be the most creative, most daring, and the most artistic. In our in our field, because today we're lacking artistry, creativity and innovation in, in the space of media, specifically in trade media in eCommerce and retail.

So what can we do that creates a prestige brand? Because that's how we're going to attract the talent. And that's how we're going to attract you know, I, I have a stretch goal and I'm going to put this out there so that one day when it happens, you guys can refer back to this on the podcast.

Like my goal right now is I want to get the secretary of commerce, Gina Raimondo on my podcast, right? I want to get I want to get people at the highest level that are the most That are creating the literal future of commerce to come and speak authoritatively at our events and to speak on our media properties.

Um, so, you know, what are we? We're a media company. And we're growing, you know, we have about 50, 000 people that are paying attention to our content. And they all are decision makers at the world's largest brands. It's. Disney, it's Sephora, it's Nordstrom, it's Westfield, it is LVMH. We have 180 people at Microsoft that download it and you listen to our podcast every single day.

It's open AI. It's, it's everybody who is doing anything in the space of e commerce or retail who are trying to see around the next corner, trust future commerce to help them do that.

Alex Love: Well, interestingly enough, so I work in government contracting and Department of Commerce is one of our biggest clients. Oh, wow. Okay. Nothing happens by accident.

no, not at all. I was just going to say from a government contracting, you know, lens, I appreciate what you're trying to do, right? Because, I live in a similar space where we do, we get to do a lot of creative things at my company and that's why I work there, but not a lot of fun things happen in that industry for, you know, better for worse.

So I appreciate that. But yeah, we can pull that commerce thread after this

Phillip Jackson: Oh, that'd be amazing

Elliot: I love how you wrap that up. The reality is you're living and breathing like an example of what these e commerce brands should be doing. And obviously, you know. Yeah, it. Today is Black Friday. You know, it's amazing.

10 years ago, you would not be sitting online right now. Any kind of a retailer or commerce person, they'd be crying in the back room with maybe a bottle of whiskey trying to survive this day. And what came before it, it's, you know, weeks and months of preparation for these kind of activities.

But, you know, you're a living, breathing example of how these brands should be facilitating. You're creating. Research reports, information acts, you know, accessibility of information that just realistically you get from like these different brands or agencies, but now you are an independent person that kind of has this platform that people can tap into, which, you know, that's eventually what I would love for Alex and I to have created here a platform for destigmatizing failure, but you have done exactly, you know, what we're aspiring to do is like that independent thing that sits in the middle and it, You know, you're able to do it in a way that just fully appeals to people.

You know, again, I, I keep hyping you up because you deserve it, but I want to make it very clear that, you know, again, all of these little nuggets of information and the way that you started from being, you know, essentially a rockstar towards you know, a brand builder, it is just such a. Zigzagging line and it's crazy to be able to see that.

Yeah. Sorry overnight success is not a thing. But maybe after 20 years that overnight success has, has, you know, appeared.

Phillip Jackson: very

like I told you before we started recording this I've been you know publicly performatively vulnerable on media of my own creation for now You know, 8, 9 years I think if you were to piece it all together, and I'm sure nobody's paid attention to everything all the way through.

So I'm the 1 constant. I know what I've said, and I know what I've done. But if you would, if you had paid attention, you'll know yeah, I had a moment where. I was profoundly overweight and very unhealthy and, you know, I was pre diabetic and I had was on an inhaler and I had to make some decisions about my health.

And, you know, it comes at a cost too, right? I've made sacrifices to be. To, to be where I am to the feeling of 16, 17 years in an industry of having everybody who do have a network from college that do have you know, college friends or people they could look to that are now, you know, big wigs at some company that gets them in and gets them that first meeting.

A lot of my network was built. You know, in the professional career and did not was not durable enough to last for decades, which is something I look at very jealously of people that do have, you know, a college network that continues to help deliver value for them in the future. My network was very much based and, you know, faith based organizations that didn't really pay off in the sense that I need it to at this point in my journey.

I do look at some of those things as like they've, they've, I think I've, I've had to, I have played from behind. And I don't know if that's an imposter syndrome. I think it's being reality. It's just, you know, checking in on reality. But I'll say the biggest sacrifice that I've made along the way, and this is, you know, in the, in the vein of failure is, you know, to have that big New York consulting job that gave me all that freedom that allowed me to operate a media process property.

I had to be away from my family for 23, 24 weeks a year. And we had young kids. You know, my kids are 11 and 12 now, and they went years and years where dad was on the road. You know, I've had you know, my, my marriage has had its share of ups and downs. We have our 20th wedding anniversary Wednesday next week.

And, you know, my wife has lived through 5 eras of Philip Jackson and where I've had to reinvent myself over and over and over again. And then that comes at a cost, right? You know, these things what I've tried to do is, you As a storyteller, because I think that that's the 1 constant of everything I've ever done as a storyteller of some sort.

I've tried to make sense of my story and to make sense of my story. I have to look for things that are. That are proof that I'm on the right path. I happen to I, I look at someone like Micah Cash and he's, you know, the, the founder of this media property called the Bitter Southerner. He's a photographer. He created this coffee table book that was called Waffle House Vistas, which is an art book of pictures taken at various waffle houses in the southeast.

Yeah. And I opened, I bought this book recently Waffle House holds a little bit of a special place in my heart because it was like the first job I had I worked at a Waffle House and, and to the fact that I, I think to myself often like, Why does that make sense for me? Like I look at something so small as that.

And I try to storytell why, why Waffle House? Why did I spend my time at Waffle House? What was I supposed to have learned through that? And it wasn't until three months ago, I walked into a bookshop and I picked up this book from Micah Cash, who took these pictures at this Waffle House. And I opened to his first essay and the essay that he writes that opens the book talks about how commerce is a democratizing force that a place like Waffle House.

Is a place where people come to eat a little bit of good food. It doesn't matter who you are, where you come from, you come to a place of equal footing and you sit in the same red booth and you're going to look out the window and you're going to no matter what out the window. You're gonna, you're gonna have the same vantage point as anyone else that has all kinds of different backgrounds and lived experiences and different socioeconomic circumstances in their life.

And actually what he's saying is that commerce is the Democrat democratizing force in the world. And that Waffle House is this like bastion of democratization that sits in the world and sits apart from the other economic realities we have. And I look at this man and I'm like. Oh, my waffle house time makes sense now because I wouldn't have appreciated that.

So I think that for me, something so small as that is I'm just trying to reconcile. I think we're all trying to reconcile like what our story is and what it means and how to get any kind of like value out of the things that often feel like side quests. And that's hopefully what I think people would be able to take away is that sometimes those little journeys didn't make sense until.

You know, much further down the road, and then 1 day, they do yeah, if I could, if

Elliot: Not to get too deep into philosophy, but since you opened that can of worms, you're basically At the line between like nihilism and absurdity where, you know, it is up to us to derive value and meeting out of whatever we do and whatever environment we're in and what impacts us and, you know, I, I personally subscribe to that same approach, you know, again, if we want to look back and you know, when I went to get a master's degree, you know, anyone could get that piece of paper.

But you all have different experiences. So I realized, you know, I did horrible at my undergrad. Like it was pure garbage. I don't know how I even got a piece of paper after that one. But when I went to go get the master's degree, it's if I'm actually going to do this and I don't know why I ended up signing up for it.

It's I have to actually pull something out of this. Can't just be memorization and just capturing and stuff. You have to be able to apply it. And I still do that today because I run mentoring programs and circles like that. And a lot of the communications stuff that I've learned was applied to that.

You know, just overly relating to what you're saying. I think, you know, being able to pull meaning out of it, it's up to us to figure out what that means. We don't have to let the world necessarily say what that means. And I love that because it ties really well into obviously what we're trying to do.

You know, failure is a road bump. It's a thing that we navigate around. It helps build us to become who we are, but it doesn't have to say who we are. It doesn't have to pull us back. And that was my soapbox.

Phillip Jackson: Silence.

that we do with retail and brand operators today I think oftentimes. It's the failure something that happens as a failure in the business that actually gives you the opportunity to have the best relationship with your customer. You know, we see this all the time in customer service and customer experience teams is people who call in for problems.

But we had the, the head of CX for Porsche was on our, our show not so long ago. And he was telling me that There's no one quite like a Porsche owner in all the ways that you can possibly imagine And that you know, some people they buy these vehicles and then they wait for months and you know Porsche has this like tracking facility where they they'll show you like here's your picture of your car being built and here's your picture here's a video of it gloating onto the the onto the boat and oh you can live track it as it's making its way along across the ocean and Oh, it's here.

It's ready for pickup and do your test drive. And they put all of this like incredible customer experience into the anticipation of taking delivery of this you know, for what is a lot of people, this you know, childhood dream to own this vehicle and then they take delivery and then there's something wrong and you can only imagine like how angry these people are and like how frustrated they can be.

And probably. In some cases, probably rightfully right. But his perspective is like the CX team wouldn't exist without that. It's actually generational brand loyalty and your kids are going to drive. Portia is how you treat it in those moments. And that failure in some way, it gives you an opportunity to outperform and outshine and go over and above.

So you have to look at it as an opportunity to do better. And that's, I think a thing I go looking for a lot of times is not like how we, yeah, I philosophize everything y'all but, but I do think it is, it is important because I think a lot of the work that we do, especially when now that brands have to move at the speed of culture is something that we say a lot, like we're going to get it wrong a lot.

Or the over 10 window shifts and the things that we did in the past are no longer culturally relevant. And sometimes they're seen as culturally abhorrent. We're going to have to like. Own our past to, to some degree we have to deal with both our past future and present now, all at the same time.

That's really hard to do as an organization. So you have to get used to being a failure. I think so. That's it's core to what we do.

Alex Love: Yeah, no, I appreciate and love all of that. Like you said, it's up to you to create your own story and make your own meaning out of things that happen, but truly believe that every place that you put yourself or find yourself, you know, teaches you something or makes you a better person.

And all of us have had the opportunity to reinvent and start over. And, you know, I think we're all doing quite well and quite successful, but who knows what the future holds and And what other failures we're all going to face and how we're going to look at it, but the resilience that you've been able to pull through your entire life to continue to reinvent and find positivity is quite amazing.

I really, really enjoyed this conversation and I really appreciate you taking the time to speak with us. So looking back, right? We're at the end of our time together, but I would love. You know, if you have one kind of singular piece of advice or something that you would pass along to entrepreneurs coming up or people looking, you know, back at their life and saying, I don't know what's next.

What sort of piece of information would you share with them?

Phillip Jackson: Well, we didn't even get into Something I think has been profoundly helpful for me. I feel like I've I've had Fewer opportunities to look at something as like a true failure since I decided to adopt a mission statement for my life. So I think it starts personally. And I, I, you know, I read this book called essentialism by Greg McCowan.

And like any. You know, it's a, it's one of those like nonfiction business books. You're going to get it in the first chapter. You really don't need to go on much, but he does have this section about creating a personal mission statement. And how a mission statement becomes a decision point for everything.

Every opportunity that comes your way to say, whether it's on mission or off mission, and you can make clear headed decisions about saying when saying yes to something is saying no to something else. I found that I feel. I feel less often like I've truly failed at something now that I look at things through the lens of, is this on mission for my life?

Or does my mission statement need to be readdressed? What is my purpose? And if I'm more cerebral and more deliberative about those sorts of things and less impulsive, then I feel like. Even if something comes out as like it didn't achieve the goal or it wasn't the objective that I set out to, you know, to to accomplish that.

I still have a framework to learn something and to learn to grow from it. Which I don't know that I would have thought about it that way. Prior to, to that, you know, transformative perspective in my life. So I, if I have to leave anybody with any sort of advice, I think that failure is all about contextualization and the, it's all about the way you look at something and what your expectations were and what your resentments are after the fact.

And you can manage all of those things. If you just have better decision criteria about what you're doing and being much more intentional about what you're doing in your life and in your business.

Alex Love: Yeah. Great book for sure. Awesome. Elliot, any final parting words?

Elliot: I do. So if you are interested in hearing more about Mr. Philip over here and his background, but realistically, if you're interested in e commerce and brand building, check out future commerce. com. their newsletter and their podcast. Even if you're not really interested in it, I would recommend checking it out anyways.

I am generally inspired by the kind of stuff that they put together and I absolutely love it. I think if you are any kind of content creator or someone who's just trying to learn and grow, looking at what they have, it's just so cohesive. Anyways, that was me overselling something. He's not paying me, I don't think, but thank you so much for joining us.

We really appreciate you being here. And being among our first season, we really appreciate it.

Phillip Jackson: Thank you so much.

Mastering the Art of Failing
Mastering the Art of Failing Podcast
Join your hosts, Alex Love and Elliot Volkman, as we dismantle the stigma surrounding failure and empower you to transform these challenges into opportunities on your own journey forward.