Our typical day/week/month

Stefan’s Head — The First Year

Mentors, advisors and friends of Stefan’s Head,

This has been a tremendous year for Kush and myself, with many ups and downs along the way. I want to take a moment to reflect on what we’ve gone through as a company, as founders and as people — and share that journey with those have helped and supported us throughout.

Goods of Record

Leading up to 2015 we formed and launched our first business, Goods of Record.

In January 2014, a Wharton classmate and I had the idea for a new take on selling men’s accessories. We observed a growing trend of men taking an interest in what they owned and how they looked. We also saw the emergence of “makers” who were crafting incredible, high quality products.

We knew storytelling would be a big component of the business, so I turned to my childhood friend Michael Kushner for some advice. I’ve always known Kush to be extremely intelligent, creative and talented. At the time, he was working as an art director at DDB, a top-tier advertising agency in NYC. I took a train up from Philly to NYC on a Saturday and we spent the day brainstorming.

That day was an important inflection point for us. Kush had hundreds of great ideas, and he showed me two very memorable videos: George’s Handmade Boots and Shinya Kimura. These were strong influences on the videos we would eventually create for Goods of Record, which include:

The same day, Kush joined the business as a co-founder. Not many people get to work with one of their closest friends since childhood — it’s an opportunity for which I’m incredibly grateful. Beyond our childhood memories, Kush and I share an appetite for adventure, risk and putting our own marks on the world.


Being accepted and participating in the Techstars Winter NY ’15 class was both unexpected and serendipitous. When we launched Goods of Record in the summer of 2014, we emailed hundreds of friends and former colleagues to announce the new company. One of these people was cody simms, my former manager at StumbleUpon and the current Managing Director of Techstars Disney in LA. He passed our info to Alex Iskold, who had recently completed his first program as Managing Director of Techstars in New York.

I had a phone call with Alex the day we launched GoR. He spent 45 minutes giving me extremely helpful feedback and product advice, not once asking for anything in return. I was blown away by his generosity and willingness to help. We spoke several more times over the next few months. Eventually, he suggested we apply to Techstars. That suggestion changed our lives.

We weren’t looking to join an accelerator, but I’m so glad we did. Techstars was a remarkable experience that forced us to think and adapt extremely quickly. We received hands-on attention and guidance from Alex and his team, and met countless mentors.

The biggest benefit of being in Techstars, besides the insanely helpful alumni network, was the compressed period of feedback known as “mentor madness,” which contributed to us changing our business entirely.

The Pivot

We met 60+ people during our first few weeks in Techstars, including start-up founders, VPs at big media companies, and people with strategic skill-sets relevant to our e-commerce business. Pitch after pitch, we heard similar feedback — that we needed to do something more distinct and develop a stronger, more polarizing voice. Deep down, we agreed with that and spent the next several weeks searching for the right way to apply that feedback to our business.

We had a couple of “lightbulb moments” during the first half of the program that ultimately helped us channel that feedback.

  1. We decided to reach out to all of our GoR customers for feedback, via sms. We texted ~250 people. Over 80% of them responded and had very engaging conversations with us. This was a shockingly high response rate compared to other channels.
  2. We partnered with The Skimm, a daily newsletter, for a customized product promotion. We generated more revenue that day than we had in several months prior. At the time, they had a 1.5M+ highly engaged subscribers. It was obvious that their brand, tone of voice, and personality drove their success.

We wanted to create a distinct voice and leverage the convenience and intimacy of messaging. Stefan’s Head is that creation.

Stefan’s Head

We started with just ~400 people on our list, designing our own t-shirts. This was one of our most popular shirts:

Dinos in Paradise

We continued to design and contract-manufacture our own t-shirts over the first few months, and all of them sold out or did extremely well. We even built some of our technology specifically with this model in mind, so that we could send on-demand orders to our manufacturer via their API.

We knew we were onto something, but looking back, we made a ton of mistakes. Many of our mentors warned us we were doing too much — creating a new distribution channel, designing clothes, fulfilling orders… it was certainly overwhelming.

We listened. Today, Stefan is a curator of cool — apparel, content, and even events.

You can check out more about our brand and the drops we’ve done here:


When initially building out a team of advisors, it can be easy to add people who look amazing on paper and have notable names or backgrounds. It’s easy to think “Holy sh*t, we got X to be an advisor for us! Investors are going to think we’re so legit!” In our experience, credentials alone won’t bring investors or value to your business.

The advisors who help the most are genuinely enthusiastic about us as founders and the business we’re building. Great advisors are there to help us succeed as founders, not to make our business look good on paper. They’re critical, but supportive, and they always celebrate our wins.

These are just a few of the advisors and close mentors who have been extremely helpful, not only when we asked, but proactively:

tobias peggs — We met Tobias in the first few weeks of Techstars, when we were still running Goods of Record. It was at the end of the “mentor madness” period in which we were giving back to back pitches for several weeks. We were tired, and honestly a bit beat down from the feedback we were receiving. We gave a fairly lackluster Pitch to Tobias and he called us out on it. Luckily he gave us another chance a few weeks later and he’s been a great mentor and advisor to us ever since. Tobias always gives it to us straight and gives us great critical and encouraging advice. He’s made countless introductions, not only to people we’ve asked for but to people he’s thought would be a good fit. Tobias actually introduced us to another one of our advisors, Paul!

Paul Budnitz — The first call we had with Paul blew us away. His enthusiasm was contagious. Paul is a super creative and positive guy and you can’t help but feed off of his energy. He’s created a ton of cool companies that we admire and respect like Kid Robot and Ello, and offered valuable advice on fundraising and building our brand. He’s always been very proactive in offering up ways to support us via Ello, as well as introduce us to the CEO of Kid Robot which we’ll be working with in the near future.

Alex Iskold — Alex has been with us since the beginning and has always been our biggest supporter. It’s obvious that he loves working with entrepreneurs and wants us to succeed. From that very first phone call in the summer of 2014 to now, Alex will make himself available at a moments notice and do whatever is necessary to help us grow. He has made more introductions than I can possibly count and is constantly brainstorming ideas for product and growth. He’s the first to congratulate us on big wins and the first to tell us when he doesn’t like something. We feel lucky to know Alex and feel bad for any entrepreneur that doesn’t have the pleasure of having him in their corner.

We will continue to lean on our advisors and mentors for help in the coming year and hope to get better at communicating with them and asking them for specific help when we need it.


In the early part of June, I decided to reach out to Giff Constable, CEO of a product development shop called NEO. As part of a side project, they created “Ask Alexis” — an SMS based service for giving advice to guys. I figured it couldn’t hurt to chat.

We had a few meetings with Giff, Chris Carella and Anil Podduturi, which turned into an invite to work out of their beautiful space in Flatiron. Those guys, along with Josh Seiden and the rest of the NEO crew were nothing short of fantastic. We took part in their weekly demo sessions and always had someone to bounce ideas off of and receive guidance from on product and strategy. They are all loyal customers as well!

The NEO team was more than generous in letting us crash for 6+ months and we could not be more grateful. We truly enjoyed our time there and hope to work with all of them again in some capacity. You guys are 💯.

(which reminds me, if anyone has space for us to crash in 2016, we’d love to hear about it 👍)


The goal for most companies coming out of Techstars is to raise a round of funding, largely centered around demo day. We didn’t take that route because we had pivoted to Stefan’s Head and were roughly only a month into the business.

In the months that followed (summer), we instead focused on iterating on the product and seeking out advisors and partners, which we felt would only help us in the fundraising process. In retrospect, we should have focused less on that and more on traction and initial investor conversations.

As fall approached, we decided it was time to ramp up investor conversations and begin to raise a round. We heard tons of conflicting advice on how much to raise — “start extremely small, 200–300K” or “anything under 500K won’t get investors excited, they’ll think you don’t understand what’s required to grow.” The truth is, we’ve heard conflicting advice since the day we began, not only about fundraising, but product and general strategy as well. We’ve learned to be more measured with how we take and interpret advice, and are no longer pulled in different directions so easily.

There have been a few people that have been extremely helpful to us in the fundraising process. One of the people that stands out is Shane Mac. Shane is the type of person you feel like you’ve known for years, even though we (semi-creepily) met through a character named Stefan via SMS. He was extremely open with sharing insights he had learned through the fundraising process of his own. We Skyped with him and 30 minutes after the call we booked a trip to SF. Shane got us super pumped about coming out west and made a bunch of introductions. This trip not only opened our minds to different types of investors (east coast vs. west coast) but also led us to one of our most important meetings to date.

Of the critical feedback we received from investors, the most common was about the growth potential of a singular brand. Many investors pushed us to think more about a SaaS model. Both Kush and I cringed at this thought. That just didn’t fit in with our vision. But looking back, we admittedly weren’t thinking big enough. Until we met Steve Jang.

On our second-to-last day in SF we met Steve — a well-connected angel with a great eye for product and thinking big. It was unlike any other meeting we’ve had up until that point. Steve got exactly what we were trying to build short term but also vividly expressed his vision of the company. We’ve always truly believed that what we’re building is special, but had never quite articulated the 5–10 year outlook. Steve Jang unlocked that for us and we now know precisely what we’re striving toward. More on that later.

We’ve been super scrappy the past 6 months, often burning <5K/month. We haven’t been paying ourselves and have had helpful friends that let us squat (thanks NEO!).

The biggest realization from this fundraising process is that we don’t need to raise a ton of money right now. We don’t need to follow the norms or worry about what our peers are doing. We’ve been able to accomplish a lot with very little.

We’re going to begin 2016 with a few strategic tests and projects, which we’ll use as proof points to raise a small bit of funding to lead us to our next milestones. Our number 1 goal is keep the business going so we can reach more people and ultimately grow into the big business we believe Stefan’s Head can become.

Emotional Rollercoaster

Everyone says that starting a company is an emotional rollercoaster.

“The highs are really high and the lows are really low” — every entrepreneur ever

Until you’ve experienced it for yourself, those are just words on a screen. Nothing could have prepared me for the emotional and psychological ride that was 2015.

We experienced crazy highs:

  • Being featured on Product Hunt our first 2 weeks in business
  • Being featured in Business Insider the very next week, bringing in 1000+ people in just a few hours
  • Being featured in Dazed Magazine, PSFK, and Complex among others
  • Techstars Demo Day
  • Selling out of our first few products
  • Meetings tons of artists, musicians, filmmakers, designers, and founders that we admire and respect
  • Making tons of friends with founders in the start-up community that we have a common bond with
  • That first investor “yes”
  • Designed a t-shirt for Wu-Tang Clan and (Kush) went on stage with them
  • Meeting with billionaires
  • Meeting and working with Justin Curhan, who helped us tremendously the past 6 months
  • The feedback we constantly get from customers about how much they love Stefan’s Head

And we’ve experienced crazy lows:

  • Letting go of our original business
  • Going through a very difficult founder transition in which we went from 3 founders to 2
  • The countless moments we realized we wasted time on certain things and should’ve been focused elsewhere

Though these events stick out in our minds as being peaks and valleys on the journey, the truth is the biggest toll is taken day to day. Some days we’re feeling phenomenal and other days we feel like we’re climbing an uphill battle that can’t be won. The back and forth is what makes it brutal, but those moments of ‘high’ will always keep us going, searching for the next small win, the next milestone, the next high.

The most frustrating part of the whole process is how un-relatable we’ve become to most other people in our lives.

Not even our significant others can understand exactly what we’re going through, but we appreciate their support and patience immensely. A thousand thank you’s to Hedvig and Nancy, who have dealt with our ups and downs, and been hugely supportive. They’ve done everything from packing and fulfillment to editing the article you’re reading now.

Luckily Kush and I have each other to share the experience and keep one another in check. Some days I’m up and he’s down, other days the opposite is true. No matter what I think it’s safe to say we couldn’t do this alone.

Other than entrepreneurs, no one can truly understand what it’s like to be out there every day with the entire weight of responsibility on your shoulders and the ambiguity of having no idea where things will stand a month from now. It’s both terrifying and exhilarating.


As I mentioned earlier, we had a meeting in SF that changed our mindset and got us to think much bigger about the business. We’ve always talked about branching out Stefan to reach other demographics, i.e. “Sophia” for women. But to be honest, we always stopped there.

We now believe this can and will be much bigger than we ever anticipated. Stefan is just one of hundreds of ‘characters’ we will create that will be experts and influencers in their respective categories. Though Stefan is objectively more urban in nature, we will have ‘Chuck’ for sneakers, ‘Jack’ for preppy apparel, ‘Kobe’ for sportswear, etc. It won’t be restricted to clothing either. Characters for music, movies, events among many others will all exist within a larger messaging commerce ecosystem. Some of these characters will even be real people or their respective brands, bringing in existing followings and customer bases to a much more accessible way of shopping and consuming content.

Just as we’ve created Stefan’s Head in the model of an ‘agency’, we’ll replicate this process over and over again within the ecosystem. Each character will have it’s own design aesthetic, tone of voice, and specific style of curation.

Stefan is just the beginning, the proof point for something much bigger that we’re excited to see grow over time.

What we’ve learned

  • No matter how successful we are or how much we struggle, we have to enjoy what we’re doing or it’s not worth it (hint: we do)
  • Communication and extreme transparency with each other is absolutely necessary.
  • Mistakes are fine, almost encouraged — as long as we react and course correct quickly.
  • The business will evolve over time as we learn new information — customer feedback, technical constraints, financial constraints, etc.
  • 90%+ of people we meet won’t be helpful. That’s perfectly fine. Focus on the 10% that are excited about the business as mentors, advisors, investors etc. It takes meeting those 100 people to get to the 10 that will be there a year from now.
  • A “no” is a great thing. Saves us time and mental energy worrying about someone that isn’t going to commit to being helpful.
  • Not getting into a grind or too much of a routine. Always evolving and always look for ways to break through the next barrier we encounter.
  • The biggest one for me — is to not ignore my health. If you’re not healthy, you’re not happy. If you’re not happy, you’re not productive. I’m making big changes this year to address this, which you can read about here.

Wrapping up

2015 was an incredible year. We could not have imagined we’d be where we’re at now, and I hope the same holds true next year.

Stefan ended the year with a Year in Review, be sure to check it out!

We’re getting aggressive in 2016.

More tests. More product changes. More iteration. More stunts.

We’ll be improving the product and the drops themselves, as well as putting out more content and more frequent texts.

We’ll be focusing on the mechanics of our customer flow — more shares, more virality, faster load times, less friction.

We’re working with brands/partners big and small to reach new audiences and get more feedback on the service we’re providing. We’ll have some exciting news to share in the coming months about a few of these projects.

Perhaps most importantly, we’re going to grow in a big way this year. We’ll grow our list 10–20x and continue to work towards product market fit. Our brand is strong, our metrics are healthy, and now it’s time to share that with more people.

We’re excited about 2016 and looking froward to sharing more updates.

We thank you all for your support and guidance and encourage you to reach out to us anytime. We love hearing from you and so does Stefan. Text him anytime, and follow him on the gram.

This article was written with my co-founder, Michael Kushner.

Update (November 2016): Thanks for those of you that have made it this far! I’ve gotten a lot of great feedback and questions since I first wrote it, and many have asked for an update. I’ll write a longer post sometime in the future, but for now I’ll give you a quick summary.

We ultimately decided to retire Stefan in spring of 2016. Though our users were passionate, we never quite hit the tipping point of growth needed to sustain the business over time. Part of succeeding is knowing when to walk away. We felt great about what we built, the community we had, and the work we created. It was all worth it for the people on Stefan’s list. We heard countless stories from people about how Stefan changed their lives and how they looked forward to each text. Someone even named their dog after Stefan!

Our team is in tact and busy working on something new. I hope to be able to share more details on that in the coming months. We’re extremely excited about what we’re building and I think Stefan’s loyal fans will be as well!