Sunday Stories 002

LA: Let’s start with your background — how’d you get started in commerce/retail, what’s your story?

NP: I sort of backed into this career. 

Out of college (Bucknell) I wasn’t sure what I wanted to do. I had a degree in economics and philosophy but not much direction. I found an Inventory Analyst job outside of Philadelphia for a startup Sports Memorabilia company that was a subsidiary of Electronics Boutique.

NP: The opportunity was exciting to me because of the sports aspect and it kept me close to my then-girlfriend who was a Senior at Bucknell. Neither the job nor the girl worked out for me, but I found out quickly that I was good at inventory. I was fortunate that my first boss and mentor showed me the ropes, and I ended up following him to another startup that was similar to Paper Source. That startup failed and I moved up the coast to NYC where I joined FAO Schwarz to help build their catalog and eCommerce channels. I met my wife at FAO, but the company was under financial stress and was purchased by Toys R Us. I was one of a handful of FAO folks that moved on to FAO. It was my first time operating in the belly of a big company which was a cool learning experience but I also realized I needed to be able to make a direct impact.

NP: From there I joined Michael Kors and spent 2 years working under the President to build their women’s apparel business in Wholesale. Afterward, I switched to the Retail side and helped scale up their fleet of stores by over 150 in 24 months. Kors went through their IPO and again was starting to feel “too big”. It was at that time that Andy Dunn was gaining traction with Bonobos. I emailed their customer service team (Ninjas) because there were no relevant job openings, but I knew I wanted to be a part of it. A few months later they reached out to me to help build their Planning function and start up their Wholesale business at Nordstrom. I spent 4 incredible years at Bonobos with an amazing team. Easily the most fun and best culture I’ve been a part of.

NP: After 4 years, Ty Haney and OV called and I figured I could really help Ty with what I learned at Bonobos. I lead Merch, Planning, Design, eCom, etc at different times with OV. Another great and different experience for OTG a rapidly growing Brand but for various reasons, it didn’t work out and I left after less than two years. After OV, I decided to leverage my experience and jump into consulting which was both exciting and stressful.

NP: This is where my Brand and Twitter handle (DigitallyNative) was born. One of my consulting clients was The Black Tux and they offered me the opportunity to join full time. TBT was a great team and business, and it gave me the opportunity to expand my universe and experience into rental which is a very unique model. TBT was unfortunately hampered by COVID restrictions so I linked back up with Andy Dunn and his sister Monica to help lead Monica + Andy. There I helped them expand into Target and Buy Buy Baby.

NP: As much as I loved M+A, the baby apparel business is brutally competitive and I started to feel stuck, so I connected with Taylor and Parker at Feat and joined as their COO which gave me the chance to lead all non-marketing functions and again take on new challenges

NP: It’s been a wild ride. Fun at times, difficult and stressful at others. Some challenges and wins overlap, but each experience has been mostly unique. I’m thankful for the journey

LA: lots of cross-category experience there. would love to dig into your operational expertise a bit.

what would you say was a common issue most of your brands ran into?

NP: Haha, where to begin!?

LA: you can give a quick blurb about each lol, or turn it into an advice thing — up to you!

NP: Honestly each Brand was different.

Michael Kors probably set the gold standard for winning. They had the Brand Visionary, Leadership Team, Marketing, Price/Value and execution very well dialed. It was a masterclass on building a global Brand and I was thankful to have a visible role in it both in terms of my impact but perhaps more importantly the opportunity for me to observe and learn

NP: Bonobos was a different animal altogether (pun). It had an infectious founder and leader, outstanding company culture, and an incredibly talented and well-assembled team. What ultimately hurt Bonobos was a bit of the cost of doing business back then (building from scratch), chasing shiny objects (Women’s Brand, golf Brand), and most critically an underdeveloped Brand that pivoted later away from its core customer

NP: Outdoor Voices was rocket fuel. In many ways, it was the opposite of the nerdy math problem that Bonobos was. It was all electricity and passion and vision. All gas and no breaks. The pressure of all of that and the expectations that come from taking on external investment could have turned it into a diamond but instead it lead to suboptimal decision-making, stress and anxiety towards the end

NP: I think if there’s one common thread from the DTC Brands is that the idea that things (CAC, profitability, operating leverage) get easier the further along you get is not accurate. They get harder and costs often scale linearly when building a digital-first Brand

NP: The other commonality is that money comes with expectations, and if and when those expectations are not met, there are consequences. VC and PE-funded environments are very different than bootstrapped. I wouldn’t say one is easier than the other, but both have serious pitfalls

LA: what was the biggest focus shift when comparing 0-$1M; $1M-$10; etc etc?

or I guess a better question would be-what do you think is the signifier of key growth shifts with brands? i.e. the above question is revenue based but what is a better indicator of a shift?

NP: I’ve never been a part of 0-1 so I can’t opine on that

NP: But $1-10M is sort of figuring out your customer and nailing the brand. It’s also about beginning to build your culture with the “founding team”. There’s not a critical mass of data or results to guide you, so it’s a lot of test-and-learn. Probably the hardest stretch

NP: $10-$100M is people, tools, process. Building the right execution engine to deliver repeatable results

NP: Beyond $100M is ‘set-to-scale’ mode. It’s about stress-testing all of the components of the execution engine and making sure you’ve addressed any weaknesses. From there it’s scale of distribution and channel. Rinse, repeat

NP: Also, > $500M is really about execution and maximizing the opportunity that scale affords you while balancing the risks presented: Inventory turn, overhead, rent, market trends, currency exchange, etc. New markets (international) are like startups within a broader engine. Different game

LA: wow this is gold. diamond. platinum level insight.

you mentioned earlier that you’re taking on new challenges with Feat. Seems you’re a fan (also maybe slightly masochistic haha aren’t we all though) of taking on tough operational challenges.

so what would you say have been your favorite challenges to overcome? At which brand(s)?

And do you have any challenges you weren’t able to overcome? How would you do that differently?

NP: I think I’ve always pushed myself. I’m a very competitive person and a lot of that competitive spirit is internal in trying to become the best version of myself and ultimately the best in the world at what I do. In order to get there, I’ve chased “time under tension”. New, difficult experiences that test me mentally, physically, emotionally, etc.

NP: MK was an interesting example. I took a pay cut to go to Bonobos, leaving a Brand (MK) that was on fire, had just IPOd and I was a rising star in the org. I left because I wasn’t excited to go to work every day. Bonobos challenged me because it felt like we were building a new business model from the ground up

NP: OV challenged me because I was now working directly for the founder and with the board. There was nowhere to hide from mistakes and I made plenty of them. It was also a challenge because it exposed me to pure creative spirit for the first time, and as a risk-averse operational minded person, this was something I didn’t handle well in hindsight

NP: Another big challenge was TBT and switching to a rental model. I came in feeling like I was one of the top 5 minds in all of retail capable of solving the rental model but was totally humbled when I realized rental is 100x more complex operationally than a linear model

NP: There were a lot of wins along the ways - many key breakthroughs that lead to success, but there were many more challenges. I gave every one of them my all, and still fell short more than I would have liked. That which does not kill us makes us stronger

NP: Also I don’t know if I’d do anything different if I got a chance to do it all again. When I look back on all of the challenges and successes, one thing I’m proud of is that I feel like I made the best decision at the time with the information available. Business is like life in this way: you cannot always predict the outcome, even if you understand and recognize the range of possibilities. Right and wrong matter much less than improvement

LA: “Right and wrong matter much less than improvement” <— that’s suchhh a major key. We can never control the outputs, only the inputs and getting better at creating better inputs. A mentor of mine early on told me that Luck is when Opportunity meets Skill, and Skill is something that you have to work for day in day out.

On Twitter Eli Weiss asked you about the cultures and learnings on how to create great cultures for each place you worked at.

Makes me curious: What’s something you learned from working with each of the brand founders? Any insights into what made each one unique?

Quick Question From The Community

NP: But regarding founders: We lionize them with good reason. They see the world a certain way, and usually, that viewpoint is unique and powerful. It’s a superpower in that they are able to convince others that their point of view creates value in the world, and it attracts resources and talent to their cause.

NP: On the other hand it’s a weakness. Their alternative viewpoint is reinforced to the point of justification. This leads to inflation of self and justification of being a bad actor.

NP: Cultures are born and cultivated from founders and CEOs, whether they like it or not. Employees feed off of their vibe and energy.

NP: Often, a founder has limited or no experience leading a team and business. These are different and sometimes opposed forces. I have empathy for the role of founder and the responsibility it bears.

NP: Perhaps that’s why I’m best suited for the role of consigliere

NP: Michael Kors was unique in his authentic ability to sell the lifestyle

NP: Andy was unique in his other worldly intelligence paired with his gift as an orator

NP: Tyler is unique in her ability to see an opportunity or trend in the future, and then manifest/create that opportunity and make people care about it

NP: Andrew (TBT) is unique in his ability to find the zen in business and in people and to make those two things connect powerfully

NP: Monica is unique in her ability to connect with people who share her experiences and make genuine connections

NP: I’ve learned so much from each of them

LA: What’s one war story you love telling?

NP: There are quite a few!

NP: My favorite winning “war story” was my second Cyber Monday at Bonobos. The year prior to when I joined, the site crashed on Cyber Monday and didn’t come back online for a few weeks. It was an existential crisis and so there was a heightened sense of importance for CM.

NP: We started preparing as a group months in advance. Part of my responsibility was to provide an hourly forecast to the team so that we could understand how we were pacing to expectations, and calibrate our stress tests to the sales volume. Cyber Monday was a big party at Bonobos. Just about everyone on the team stayed through midnight — answering phones, responding to texts and email from customers.

“We started preparing as a group months in advance.” <— If Bonobos was prepping for BFCM that early, you should too. Read Commerce Chronicles 003 where we cover a few projects you can kickstart now to get a head start on the sales push. Thank us later 🙂 

NP: As the night went on, it was clear we were pacing close to forecast — which was $1.725M for the day (the year prior we did a “Midwest Million”: $850k. We crossed my forecast at 11:58 PM and we had a live dashboard broadcast on the wall. Everyone went NUTS. It was silly, but it was such a great moment and really stays with me as to why eCom can be a drug

NP: Another war story involves my industry hero: Mickey Drexler. While I was at OV, Ty told me that he was getting involved as an investor. I thought that was incredibly cool. Bonobos was full of Mickey disciples and I knew his approach to business inside and out from them.

NP: For me it was an opportunity to go toe to toe with my hero and an industry legend. He had earned the moniker “Merchant Prince”, and frankly I wanted to beat him at everything. Fast forward a few weeks and I was meeting the Michael Jordan of retail. Moreover, he decided to work from the OV office and we literally sat across from each other. Mickey didn’t like me from the jump (this is my perspective, I have no idea the truth).

NP: Later, when I was in Austin he would fly down to the Austin office for Selling reviews. I had been through these very often at Bonobos and knew exactly how to respond. He put me on trial in front of the OV team for hours, and I was prepared like I was on trail. I sparred with him intellectually and as I recall it I held serve. It was like going 1:1 with MJ in the half court and being competitive. Later, my time at OV ended shorter than I would have liked. They say you should never meet your hero. The relationship didn’t go how I would have liked but I respect him greatly still.