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Author: Josh Payne

4 Leadership Lessons for Founders After Running a Startup for 5 Years

4 Leadership Lessons for Founders After Running a Startup for 5 Years

This time five years ago, I founded StackSocial, what is now StackCommerce. Each year for the past four years I’ve shared a few lessons (Year 1, Year 2, Year 3, Year 4) for other founders who are on the same arduous path. It’s been humbling, it’s been exhilarating, and I’ve grown in ways that I couldn’t have imagined. This year I’m back with 4 more leadership lessons I’ve learned over the past 12 months … perhaps the most important ones thus far.

Before I get to that, I want to give you a few highlights (#humblebrag) of my team over the past year.

StackCommerce Turns 5!

5th Year Highlights:

  • Grew the team to 60+ people while remaining profitable (on just $800k of capital raised in 2012)
  • Built out an incredible management team with experience from companies including Google, Gilt, Fab, Headspace, and Pivotal Labs
  • Expanded into our 4th Vertical: 1. Tech, 2. Men’s Lifestyle, 3. Education, 4. Women’s Lifestyle … with plans for 5th.
  • Grew our user community by nearly 50% to over 3.5 million registered members
  • Adopted five insanely rad office dogs: Bill Murray, Kiley, Cowboy, Zooey, and Uni

But, beyond all of that, the biggest highlight over the past five years is that we’ve not only created a successful company, but also a culture, a family, and a movement. I couldn’t be more proud of the blood, sweat, and tears that this team has put forth to help better the lives of our vendors, publishers, and customers.

Now, as promised, here are 4 lessons learned over the past year:

1. Empathy is the most underrated virtue of leadership

Like many entrepreneurs, growing up in my 20’s I revered Steve Jobs. I admired his take no bullshit, take no excuses, accept nothing but the best, and demand perfection, slant on life. I expect it of myself and so, why shouldn’t I expect it of my team? Shoot for the moon and worst case you end up in the clouds, right? But, with people, that’s not always the case.

Perfection is a tough standard to meet.

Putting that standard on yourself is your right. It’s probably not a smart one in the long run, but if you want to live with high bouts of anxiety, tension, and stress in pursuit of your ultimate satisfaction — that’s your right. But to project that onto others in pursuit of perfection often times causes us to remove all sense of “understanding” of someone else’s circumstances. That lack of empathy can hurt. It can really alienate people in a way that you may not foresee.

I’ve had some major setbacks in my life and as painful as they were — they have been a great asset to me. They taught me how fragile the human spirit is and in those moments how much we all need comfort, understanding, and encouragement … not a hard-ass with unreasonable expectations. Finding an acceptable balance in the pursuit of greatness and empathy with yourself and your team will help you endure because, frankly, you are nowhere near as good as Steve Jobs, so stop trying to mimic something you are not.

StackCommerce Full-team Offsite in Topanga, CA

2. Communication is the antidote to almost every problem

Setting up formal feedback loops should be a top priority. When you are smaller, informal 1:1’s, happy hours, and one-off meetings can be enough to get a sense of people’s thoughts and give them the opportunities to let you know their thoughts. As you grow, implementing consistent channels for frank and/or anonymous feedback is vital to staying aligned with your team. Some of the things we have done this year include:

  • Management OKR Process — Quarterly Objectives and Key Results help align the entire organization behind the top metrics and KPIs. You’d be surprised how misaligned folks are until you get everyone in the same room. This also allows lower level managers to gather feedback from the bottom-up to help build consensus on what’s important to them.
  • 360 Degree Reviews — Everyone in our org gets anonymous 360 degree reviews from peers, their direct reports, and the layer above them. We’ve found that this can surface incredibly insightful feedback that helps the individual to understand how their actions are helping or hurting not only those that they report to, but everyone in the org.
  • Team Off-sites — Last November, we took the entire team on a 3-day cruise to Mexico. (WTF…I know, right?!) But, the investment paid for itself and then some. There’s something magical that happens when you get everyone out of the office. People relax…they let their hair down a bit and they get honest. And there is gold in those moments of honest, direct feedback. I’ve probably learned more about what my team thinks about the leadership of our company in those few moments then all my 1:1’s combined. Do not underestimate the importance of spending time away from the office as a team.

3. Have a non-business mentor

I have a team of awesome advisors and investors who are phenomenal when it comes to startups and tech. And when I have a business question….they are who I turn to. But, often times, the issues I have as a founder can’t be resolved in an excel spreadsheet. They are matters of the soul.

This job will rip you apart. It will bring you to your knees. I don’t care if you are Elon Musk or Marissa Mayer or Mark Zuckerberg … you feel pain… you have low days, low weeks, and, yes, even low months. The highs are higher than you can imagine and the lows are pretty low.

If you don’t have a personal, non-tech confident you can turn to — make it a priority to get one. Today, my wife and my dad are the two people I turn to when I’m at my lowest. And, everytime, without fail, they are there for me with doses of reality, empathy, and love.

Before I was married, when we were first starting launching Stack, I was really up and down based on the momentum of each day.I took every single day personally, and when you’re in that state, you need someone to vent and to let go. In those early days, I saw a therapist and it was the best thing I could have ever done. It helped so much that the therapist knew nothing about tech, because at the end of the day, my problems weren’t about tech, they were about emotions and feelings. Many of our problems are internal and not external as we might think. I encourage you to find someone, anyone, outside your tech circle to talk to and just let go.

4. Cash is King

Every startup has a different track. Ours is what I’ve coined as being “Seed-Strapped”. We raised a small Seed round of $800k back in 2012, but we’ve been profitable ever since so we haven’t needed to raise more funding. We’re not a completely “bootstrapped” startup, yet we also haven’t raised large rounds of institutional capital. Those two facts make a very unique creature in the startup world, but it’s a path that I would personally recommend.

Raising a Seed round gave us access to new potential partners, press, hires, and social capital that we needed to grow the business and it was well worth the dilution. But, instead of going the traditional route of raising more capital and further diluting my ownership and that of my team’s, we focused on staying cash flow positive.

Some may say it was a mistake and we could have grown much faster with capital, but I also know many hooks that come with that money. Hooks that I didn’t believe were a worthwhile trade-off. Easy capital does not equate to success and, in fact, can lead you to your demise by allowing you to go too fast too early before you figure out product-market fit. We’ve seen this all too often. Founders think that raising capital is like putting training wheels on a bicycle, but It’s akin to slapping a rocket on a tricycle.

Raising some capital gave us the connections and PR without the baggage and dilution that comes with raising large rounds of institutional money. The downside of this is that you have to be more disciplined in your spending. While your competition is moving into that shiny new office at $6.50 sqft/mo…you may find yourself subletting from their neighbor.

Regardless, the ability to stay independent, make your own decisions, and have your own path is invaluable. Take on capital wisely, even if you can raise more. I would advise you to take what you need and, if you can, get to profitability ahead of growing a few percentage points faster. Maybe that’s heresy in the startup world, but I’m a bit cynical after seeing too many startups grow quickly and fade even faster.

Here’s to the next 5 years. Good luck and Godspeed.

Announcing Our Expansion into the Lifestyle Vertical & Introducing Citizen Goods

Announcing Our Expansion into the Lifestyle Vertical & Introducing Citizen Goods

After four years of focusing exclusively on tech products and publishers, we are thrilled to share that StackCommerce will now be offering our native commerce solution to lifestyle publishers, launching with a stellar list of partners including AskMen, theCHIVE, Digg, Rant, The Awesomer, Everyday Carry, and over a dozen others. These new partnerships expand our reach to more than 200 million unique visitors per month, and open an entirely fresh commerce opportunity to current and future partners.

We would also like to officially introduce Citizen Goods, our brand new lifestyle marketplace featuring curated modern products across home, outdoor, grooming, everyday carry, and apparel categories. Citizen Goods is the destination site for our lifestyle-focused partners that prefer an affiliate solution rather than an integrated Shop. To support Citizen Goods, we’ve also launched amazing new product features that allow for further customization of Shops with adjustable homepage heros, content modules, fonts, and navigation. With more advancements in the pipeline, we will continue to deliver innovative ways for our partners to truly personalize the look and feel of their Shops.

Native commerce is clearly resonating with tech and lifestyle audiences, as our member community within our network of Shops grew by 250% to more than 2.5 million members over the past year alone. The overall effectiveness of Shops is also increasing, and we’re proud to see publishers averaging six-figures of gross sales annually, and top partners generating well into the seven figures. This demonstrates the proven success online media sites have found with native commerce as a new and incremental way to monetize their content.

We believe this expansion comes at an ideal time for lifestyle publishers given the rise of ad blockers and decreasing effectiveness of banner ads. The key factor is that truly native commerce works not only from a financial standpoint as an alternative to ads, but also adds brand value by turning readers into loyal buyers who appreciate access to exclusive commerce content. With native commerce, we also eliminate the need for publishers to manage operations, shipping, sourcing, and customer service so they can focus on creating impactful content for their readers. We will continue to expand further into new verticals in 2016, pursuing our mission to revolutionize content and commerce across all online media categories.

Native Commerce vs. Native Advertising: Which One is Better for Your Brand?

Native Commerce vs. Native Advertising: Which One is Better for Your Brand?

You may be wondering how Native Commerce compares to Native Advertising, or perhaps whether Native Commerce is a type of Native Advertising. Rest assured, the answer to the latter is “no” — Native Commerce is its own beast, and it comes down to one crucial difference: Native Advertising primarily benefits brands while Native Commerce focuses on content creators.

Let’s think about Native Advertising and what it, in the most basic form, actually does. Ad exchange service Sharethrough defines Native Advertising as “a form of paid media where the ad experience follows the natural form and function of the user experience in which it is placed.”

Essentially, Native Advertising allows brands or content creators (through services like Sharethrough) to more seamlessly integrate their marketing and / or products into your content, with the intention of driving prospective buyers or readers away from your site. Breaking that down:

  • Making brands more likely to want to advertise to your audience — great!
  • Blurring the lines between your own content and that of an outside brand — not so great.
  • Taking your users off your site — bad, bad, bad.

Even the first point isn’t a real selling point. Brands always want to advertise with publishers that cater to the same audience — Native Advertising just makes it easier on the advertiser’s end.

Now let’s compare this to Native Commerce. Native Commerce allows publishers to seamlessly and organically integrate relevant products into their own content, so they own the customer’s purchase cycle from start to finish — from discovery to desire to checkout. Breaking that down:

  • Selling products directly through the content you’re already producing — great!
  • Monetizing in a completely transparent way that gives users direct access to products when they want them most — wonderful!
  • Keeping users on your site to buy instead of sending them somewhere else — hooray!

If you’re trying to figure out new, innovative ways to generate revenue from your site, don’t always feel like you have to give someone else center stage. With Native Commerce, keep everything under your brand — and generate more revenue — in the most seamlessly integrated way possible.

StackCommerce Year in Review, By The Numbers!

StackCommerce Year in Review, By The Numbers!

It’s been a great year for StackCommerce! Here’s what happened in 2014, as told via the numbers:

1.13M Orders Placed on the StackCommerce Network

1.4M Members Across the StackCommerce Community

200+ NEW Publisher Partners Including Business Insider, BGR, The Next Web, Slashdot, Android Authority, & Joystiq

300+ NEW Vendor Partners Including Rosetta Stone, NBC, Dashlane, Hubsan, DJI, Adobe, iDrive, Leap Motion, Ouya, & Shutterstock

100+ Million Monthly Unique Visitors Reached Across the StackCommerce Network

42,719,449 Deal Pages Viewed

3X Sales Growth from 2013 Holiday Season to 2014 Holiday Season

Top 5 Deals

Top Selling Bundle
The Name Your Own Price Learn To Code Bundle

Most Popular Freebie
The Mac Freebie Bundle 3.0

Most Popular Giveaway
The Epic iPhone 6 Giveaway

1 Company Rebrand
StackSocial Rebrands as StackCommerce to Double-Down on Native Commerce

33 People on the StackCommerce Team (28 pictured!)


4,455+ GitHub Commits 


3rd Birthday Celebrated


1 Mural Painted in the Office


Full Remodel of Office


1 StackHacks Hackathon


8 Surfboards & Paddleboards in Office


1 New Kegerator in Office


Thank you to all of our partners, friends, and to our families for making 2014 successful. We are looking forward to big things in 2015!


What Defines Native Commerce?

What Defines Native Commerce?

At StackCommerce, we refer to ourselves as a “native commerce” company, but what does that term actually mean? Furthermore, what exactly is involved when a publisher integrates native commerce into its online presence? How does native commerce differ from native advertising and “regular” e-commerce? Below is an overview of native commerce as we see it in 2014.

The intersection of content and commerce

In the simplest explanation of the concept, native commerce is the integration of e-commerce into the user experience of content sites or other non-commerce properties. This can take several forms and will vary based on the publisher, content and products involved. Possible integrations include:

  • running a companion store for alongside the content site that allows users to buy products from within the same brand
  • providing users with avenues to find and buy products from within or around site content
  • incorporating product links or widgets within reviews or editorial content

By providing consumers with the means to buy products they are already looking to learn about, discuss and engage with on niche content sites, publishers can close the loop and position themselves to best capitalize on their audiences.

Hyper-relevant, contextual products

A critical part of truly native commerce is the integration of products and consumer experiences that are specifically tailored to the user experience associated with a certain site. It’s the right products in the right place place at the right time.

For example, let’s say that is a content and community site where fans of different soccer teams can read content and news, and argue and debate on forums. A few key ways to describe this consumer would be:

  • very interested in soccer
  • passionate about their favorite soccer team
  • actively spends free time following/watching/playing soccer

Based on the characteristics of this particular target demographic, the obvious productopportunities are soccer jerseys for popular clubs, soccer equipment and even tickets for soccer matches in their area. All three products are clearly things that KickSoccer users will want to buy and, unless KickSoccer offers them the opportunity, go elsewhere to purchase.

An extension of your brand, not an interruption of it

One of the biggest concerns with advertorial or sponsored content is that publishers are essentially renting out the most valuable real estate on their sites to another brand. This is of particular concern with native advertising, but with native commerce, publishers can be innovative and helpful by providing access to highly relevant products and deals. As long as the writers, videographers and other content creators would genuinely recommend the products editorially, the integration of content and commerce can truly be seamless.

Let’s use the KickSoccer example again — if there is a great new soccer cleat being released and a KickSoccer writer gives it an authentic, raving review resulting in many of their readers wanting to buy it, KickSoccer can provide a better user experience by allowing them to quickly and easily purchase the cleats right from their website. No comparison shopping, no searching for a trustworthy online store  — they can purchase directly from KickSoccer, a brand they already trust. This is native commerce — targeted, relevant products and deals delivered to eager audiences in an organic way.

StackCommerce – Pioneering Native Commerce

StackCommerce – Pioneering Native Commerce

After 3 years of building both an amazing consumer experience and a full-service commerce platform for publishers under the StackSocial name, we are extremely excited to announce that, as of today, we will be moving forward as StackCommerce, with our StackCommerce-powered store continuing as StackSocial. Our goal is to completely revolutionize the way that content is monetized online, and we want our brand to fully reflect that mission.

na·tive com·merce  (ˈnāt-iv kä-(ˌ)mərs’) : the organic integration of relevant product recommendations into the content experience

This move comes as a result of the extraordinary work and results produced by the StackCommerce team — we now service over 1,000,000 registered members, power commerce for over 500 publisher partners, and have processed hundreds of thousands of orders across almost 1,500 deals — and everyone here is hungry to achieve even more.

Today’s online publishers face serious obstacles all around them, as well as tens of thousands of new sites popping up every single day to compete for users. Display ad CPMs are stagnating, the subscription model is all but finished, and fewer and fewer properties have the resources and clout to pull off events. Providing a high-quality, relevant commerce experience is the way for publishers to best monetize their sites and engage their users, and StackCommerce is the most scalable, profitable native commerce platform on the market, having pioneered the concept itself.

We’re not stopping there — being the best on the market isn’t good enough for us. We will be constantly enhancing and optimizing our native commerce platform to deliver the best possible product to publishers and meet the challenges of this ever-evolving landscape. From more customization options to expanded product offerings to enhanced customer insights — we want to do it all. This is the start of a whole new chapter, not just for our company, but also for native commerce, and we are so excited to embark on this journey with all of you.