Finding Your Edge

No one wants a watered down Tesla

I want to talk about product design and positioning as it relates to Elizabeth Warren dropping out of the race. This is not about her politics (though I was a fan) but her brand as a candidate.

Promoting a political campaign is not unlike marketing a new piece of workout equipment or messaging app or podcast. How do you stand out and grow your audience?

Seth Godin (who we spoke about last time) talks about the idea of edge as “a free prize that has been shown to make a product or service remarkable”

His recommendation for marketers and makers is to go “all the way to that edge—as far from the center as the consumers you are trying to reach dare you to go.”

If this was a normal product, it might be a quality like speed, reliability, popularity, intensity.

For a presidential race, the edges were a little different:

  • The most unique identity went to Mayor Pete, the gay military vet Rhodes scholar from the Midwest
  • The most futuristic ideas went to Andrew Yang with his focus on robots, automation, and universal basic income
  • The most focused on climate change were Govenor Inslee and Tom Steyer
  • The most spiritual went to Marianne Williamson (remember her?)
  • The most biggest spender went to Mayor Bloomberg

In a normal marketplace, each of those edges would do well among some group of the population and they could all succeed on some level. But a primary needs to collapse to a single winner, and that means that certain edges matter more than others.

Given its politics, it appears the edge that mattered was your position on the political spectrum. Bernie clearly owns one edge – there is no candidate who is further Left than he is. And Biden, ironically, owns the other edge, as the most well known moderate / centrist candidate.

Warren was more progressive than everyone except Bernie, but slightly more willing to compromise on implementing her big ideas. That’s like coming out with an electric car that’s not as cool as a Tesla but a little cheaper. That’s a bad position. The customer either wants the Tesla or they get the Prius or Civic.

Warren didn’t have a clear edge. She waffled between her fighter persona and her unifier message.

Look, I’m not a political pundit and there are probably a bunch of other reasons for why her campaign wasn’t able to punch through. Misogyny and sexism for one.

Despite being the most informed and prepared candidate in the race, it looks like this one wasn’t in the cards. It’s an important reminder that you have to have a sharp, distinct edge if you want to capture people’s attention and win their hearts and minds.

Find an edge for your product or suffer the consequences.

Quit or Stick it Out

Book Notes on Seth Godin’s The Dip

I love Seth Godin’s books and his blog. I think he’s just incredibly good at articulating distinctly memorable ideas backed by both data and stories in a way that we could all learn from.

Godin, more than just about anyone, understands both the power of technology (he’s founded several technology companies, including an early direct marketing co that he sold to Yahoo) and how technology has shaped markets and human opportunity.

I took these notes back in 2008 and rediscovered them recently. A lot has been paraphrased but there are some direct quotes as well. Bolding is mine.

The Dip: A Little Book That Teaches You When to Quit (and When to Stick)

The Dip’s Big Idea

Don’t be afraid to quit the wrong stuff and have the conviction to stick with the right stuff because being “the best” (in a given market, category, etc) is worth it.

On Being the Best

  • Vanilla is far and away the top ice cream flavor – 22% of all sales, (Chocolate is 8%)
  • The top movie of the week usually has 2x the ticket sales of the 2nd movie
  • Being the best in the world matters – no one wants an average product or service
  • Yet it’s easier to be the best in something than ever before – so many micro niche markets exist today
  • Jack Welch and GE – part of the transformation was making only #1 or #2 acceptable
  • Superstars – agents, dealmakers, artists, etc, get way more than everyone else, because they are the best
  • Average is for Losers – quit or be exceptional – those are the only two choices

On the Dip

  • The Dip is the hard part, the “moat” the prevents most people from being the best
  • The Dip is organic chemistry, law school, agent rejections, the last few pushups
  • Successful people don’t just “just ride out the Dip…They lean into it, changing the rules as they go”
  • If it is worth doing, there is probably a Dip
  • Woodpeckers don’t diversify – they peck one tree 22,000 times to get dinner
  • Men’s Health cover models pushed through the Dip to get washboard abs
  • Being mediocre sucks – and so many people and organizations have simply settled for this
  • The space shuttle is not a Dip, it’s a cul-de-sac, because it’s going nowhere and NASA needs to drop it (editor’s note – and eventually they did!)

8 Dips

  1. manufacturing on a larger scale
  2. growing a sales team
  3. getting more education
  4. taking a risk to venture big
  5. investing in a longterm relationship
  6. giving up ego/control
  7. reshaping one’s worldview
  8. getting your product into better distribution channels like Walmart.

Further Advice

  • Market acceptance is a big Dip, but worth pushing through
  • There is a difference between quitting a tactic (action or behavior) versus quitting a strategy (or long-term goal/outcome)
  • Don’t quit in the Dip – push through short-term pain by visualizing the great long-term results – AKA no one quits the Boston Marathon at mile 25
  • “Never Quit” is a terrible piece of advice but “Don’t quit something with great long-term potential because of the stress of the moment” – much better advice!
  • Michael Crichton quit medicine after graduating Harvard Med and doing a prestigious fellowship. If he can quit – so can you.
  • Before quitting ask yourself
    1) Am I just panicking, scared or hurting? All three are bad reasons to quit.
    2) Who am I trying to influence? A single person is hard to bring around, but a market is almost always climbable.
    3) Am I making measurable progress? As long as you are making some forward progress, there is hope.

Final Thoughts

  • You are astonishing – how dare you waste it on half-assed efforts.
  • Quit mediocre things and use that additional energy, time and resources to assault the Dip that really matters. Make a dent in the universe.
  • It’s almost impossible to over-invest in becoming the market leader.
  • Last page:
    “All are successes are the same. All our failures too.
    We succeed when we do something remarkable
    We fail when we give up too soon
    We succeed when we are the best in the world at what we do.

Adaptability is No Joke

Both startups and improv are about making shit up on the fly

I recently participated in an “Improv for Entrepreneurs” workshop run by Mary Lemmer, a founder-turned-VC who now teaches improv to companies and professionals. I’ve done a couple of these types of workshops over my career and seen a few improv shows — they’re really fun. Improv is like freestyle rap or live jazz: it might not be as polished as a studio album track, but it’s impressive and enjoyable to watch someone make stuff up on the fly.

If you like comedy but haven’t seen any improv before, I’d highly recommend it. Try taking a class or a workshop too. It’s hard to explain why improv is so funny, but here’s a 3 min scene (i.e. a contained performance) of first date where two actors play the guy together by “speaking with one voice“. It’s hilarious and also clearly challenging.


1. In our session, Mary had us write down leadership challenges we were facing. We started with a few exercises like Zip-Zap-Zop and Alliteration Intro. Similar to how you stretch and do a light jog to warmup before a run or workout, improv requires an emotional and mental “warmup” to get people in a chatty, creative, and open state of mind.

Then we did some improv scenes, which had as their prompts the leadership challenges we outlined earlier. I was in a 4 person group and our prompt was the one I had written down (launching and iterating on a new product). Except in the scene it was a sex toy, a much more salacious topic.

2. The first and perhaps only true rule of improv is “Yes, and“, meaning when your scene partner says something like “Isn’t it such a nice day outside?” you don’t negate them and say “No, it’s freezing and awful.” but instead build on it by saying “Yes, and the snow outside is perfect for skiing” (if you wanted to avoid the cliche sunny day situation).

But one of the other lessons / rules Mary introduced was “Play the scene that you’re in”, which similarly means, play the role that you’re in. If you’re not the “main character” of the scene, don’t try to force yourself into that position. That doesn’t mean be passive, but play the “supporting” role you’re in to the best of your ability. And in short order, you’ll probably see a moment to really shine / reshape the dynamic.

3. They say that doing a startup is like jumping off a cliff and building an airplane on the way down. You have to make up a lot of things along the way. In that regard, there are a lot of similarities to startups. Time is urgent—you can’t stop for 2 minutes to think about what you’re going to say next in a scene any more than can you deliberate for 6 months on how to go to market with your product.

Fundraising is very much a dance of improv. You play hundreds of scenes with roughly the same prompt (pitch yourself and your company) but a different partner and varied settings. You have to adjust on the fly based on how your partner is responding to you.

4. We played a game that night where you had to deliver “a report” to someone with a specific tone / energy (excited, disappointed, scared, angry, up to you) and you then had to swap place and receive the report from someone else, while maintaining your original emotion.You quickly realize that emotions are contagious. If you start out happy but the report deliverer is angry, you either become angry too or scared. Learning to both stay in character and respond to someone else’s emotions is tough. But probably valuable.

Similarly, I remember a pitch meeting where the partner looked completely bored with what we were doing, had no questions and it was really hard to stay excited during the pitch. My cofounder and I thought the meeting was a bust, but they ended up investing! I guess the lesson is that your enthusiasm matters even if you aren’t getting much back from your partner.


If you’re a founder or work in a field that’s going through a lot of change, it might make sense to get better at making shit up. Improv might be one way to shake yourself loose from old patterns and get more comfortable taking social risks that can pay huge dividends in the marketplace.

Photo by Simon Migaj from Pexels

Recharging is for batteries, not people

Why working less isn’t the answer to burnout at work

Last year, journalist Anne Helen Petersen wrote a widely shared piece in Buzzfeed naming millennials the “Burnout Generation”. According to Petersen, we’re overworked, underpaid, and often paralyzed by the systemic dysfunction of our increasingly volatile world. As a result, many of us struggle with even the most basic tasks of “adulting,” like paying bills or registering to vote.

One year later, things seem worse than ever. Wages have continued to stall, the U.S. is on the brink of war with Iran, and raging wildfires have killed more than a billion animals in Australia. Fifty-seven percent of tech workers are currently experiencing burnout, according to a survey conducted by Blind of 11,500 workers.

So what can we do to stave off or recover from the feelings of burnout in 2020? The most common advice for dealing with burnout boil down to “work less.”

We are encouraged to work fewer hours, take a relaxing vacation, stop bringing work home, and to invest in self-care. We talk about “recharging,” as if we’re machines whose batteries have been depleted. This mental model makes sense when most people were employed in labor-intensive agricultural or manufacturing work. But the analogy is flawed when it comes to white-collar workers in tech, business, or professional services.

While the term “burnout” is often used loosely in casual conversation, most formal definitions state that feeling tired is only one of three dimensions. (The other two are negativity and cynicism, and reduced sense of professional efficacy.) Working less is only part of the answer.

As I’ve written in the past, I’m very much against late-night emails and working excessively long hours. But in my view, the two other dimensions of burnout aren’t caused by a deluge of work but rather a dearth of meaning. 

I have seen many entrepreneurs work day and night to build something they believe in, exhausted yet exhilarated. And I have seen those same founders struggle to write a single line of code after hitting a major setback or losing faith in their business. Work in of itself is not the issue; it’s the meaning that the work provides.

Traditionally, people have found meaning in their lives through family or religion. And while more millennials are living at home than ever, largely due to economic reasons, they are marrying later and having kids later (if they have children at all). Meanwhile, three-quarters of baby boomers describe themselves as Christian while only half of millennials do, with 40% identifying as spiritual “nones.”

This leaves work as the primary source of meaning for many people, which can create a vicious cycle. Feeling burned out leads to poor performance, which leads to a further loss of meaning and more burnout.

In these situations, simply taking a long weekend off to “recharge” can feel like breathing on your freezing hands in the wintertime — temporary relief at best. If you’re struggling with burnout (or someone you know is) here are 4 ways to break the cycle and regain a measure of meaning inside and outside of work:

Get into a hobby

Smart and ambitious people like learning, tinkering, and making — and often burnout occurs when they can’t do that at work. If that’s the case, picking up a hobby that lets you use your natural strengths in new ways can be a godsend.

Marketer by day? Try your hand at standup comedy or maybe organize a mini-conference or event around something you care about. Software engineer? You might enjoy messing with DSLR photography or physical electronics. These hobbies return a sense of accomplishment and autonomy that’s often missing from your day job.

Reconnect with others

Weak social ties are as harmful to our health as being an alcoholic. Spending time with close friends reminds you that you’re a worthwhile person beyond your work life, and meeting new people can be invigorating.

You may be surrounded by people at the office, but unless you have a trusted best friend at work, it might be good to seek connection outside of work.

Consider starting or joining a social ritual. Whether it’s board game night, morning yoga, or a weekly multifamily dinner, like author Nir Eyal organizes, these activities ensure that you’re getting quality social time on a regular basis.

Reframe your goals

In a world of moonshots and billion-dollar opportunities, it can be natural to aim for massively ambitious goals for your career or company. But when you’re burned out, those goals can feel less carrot and more stick.

Harvard professor Teresa Amabile studied the inner lives of creative teams and found that facilitating progress, even in small increments, was the most important aspect to worker motivation.

Are there ways you can remove even minor annoyances for yourself or your team? What is a small, long-standing task that might feel good to check off? Make sure to sprinkle these into your to-do list. Outside of work, learning a new skill, hobby, or language can also provide a real sense of progress.

Find ways to contribute

One of the key psychic benefits of work is the feeling of contributing to something greater than yourself. But sometimes, you may not agree with your company’s goals or feel your own role is pointless or redundant, as a third of people do. This is one of the biggest risk factors for PTSD for combat veterans after leaving the military. War journalist Sebastian Junger writes “humans don’t mind duress, in fact they thrive on it. What they mind is not feeling necessary.”

If moving to another, more meaningful job is not an option at the moment, make yourself useful in other ways. Offer your skills to a nonprofit organization, help out friends or family members going through a difficult time, or support on a political campaign or cause you believe in. Remembering that you can do good and have an impact is important, especially when work is burning you out.

It’s great to see society engage in a larger conversation about the level of social safety net and economic security that governments and businesses should provide for their people. But irrespective of how that conversation goes, the relentless pressure of capitalism and technological change mean that millennials should expect many decades of hard work ahead of us. By reorienting our lives toward meaning, we are more likely to not just endure, but excel, in the years to come.

How ClearBrain’s CEO Used These 7 Lessons to Create a New Product Category

Bilal Mahmood is cofounder and CEO of ClearBrain, a Y Combinator backed predictive analytics company that’s used by firms like Chime Bank. He’s also a good friend of mine and someone I greatly admire for his resourcefulness and resilience (important traits for any founder!)

Bilal’s company recently launched a product called Casual Analytics that uses a new algorithm that can automatically distinguish causation vs correlation, without running an experiment. I thought it would be a good opportunity to ask him about how they identified the need for this product, what problems they faced building it, and what they’ve learned from the experience so far.

Even if you don’t really care about analytics or data or AI, this will still be an interesting interview in terms of building a great product and navigating the challenges of entrepreneurship. I’m still thinking about his 7 lessons as they apply to my own company, and I imagine you’ll find them useful as well.


JS: You’ve been building products in data analytics for some time now, starting back at Optimizely. Maybe we can start there — what were you working on then?

BM: I started as the PM of the Data Science team at Optimizely, an A/B testing platform. What data science meant at Optimizely was about analyzing product utilization and forecasting key goals.

JS: So you’re at Optimizely and you’re helping the company understand its own business through your analysis of the data. Where did this lead you?

BM: Working on data analysis at Optimizely helped me see a bigger opportunity. We would build these predictive models for our marketing and sales teams. 

But the next question was always “Why? Why are my users going to churn? Why do users go from low probability to high probability?” Etc.

This is a super hard problem. Understanding the why behind an action requires understanding what causes it in the future, versus correlated to it in the past. The tools at our disposal at the time, Google Analytics and Chart.io were insufficient in distinguishing between the two. 

JS: That’s interesting. Google Analytics is used by millions of websites. Why isn’t it good enough to handle this?

BM: Traditional analytics tools can only tell you things that happen in the past. They analyze behaviors that happened prior to someone doing a specific action – signup, purchase, etc. 

And they then use those behaviors as a proxy. Like – “Okay, people do this more before someone signs up, that must mean that it’s maybe causing them to sign up.”

That’s not really true. That’s correlation, not causation.

JS: So then you started ClearBrain, to solve this problem of predicting causation?

BM: Not immediately.

When we first started ClearBrain 3 years ago, I didn’t actually know how to completely solve this problem. I did know that it needed two components – a technology to automatically predict any outcome, and an algorithm that could specifically predict causation.

I focused on the technology first. We built a custom domain-specific language to translate any data type into a machine readable format. Effectively a universal schema for machine learning.

JS: I’ll be honest, that sounds a lot like a technology searching for a problem, no?

BM: Haha, yeah it did snowball kind of into that.

It is a super cool technology, and we even filed a patent on it. But I’d say its also the first mistake I made without realizing it.

Startup wisdom always says “Solve a problem, not a technology”. I did think I was solving a problem by automating machine learning. But it was my own problem, not a customer’s problem.

Lesson #1: Don’t just invent technology—solve a customer’s problem

Automated machine learning by itself wasn’t useful. It’s only useful if it solves a customer pain point.

JS: So how did you find the customer pain point for this technology?

BM: I reflected back on the inspiration for starting the company in the first place.

The inspiration again was that while I was at Optimizely, our marketing and sales teams were asking which users were most likely to sign up, and also why they were most likely do so.

I still thought the latter question was too hard to answer, so I focused on applying the ML technology we built to help with the former.

JS: That sounds like lead scoring. Predicting which users were going to do a certain action. That was the new direction?

BM: Effectively yeah. But that sort of became my second mistake, namely market size.

We had converted our technology into a product which we called predictive audiences. We used our automated machine learning platform to enable any business stakeholder to build any audience by their probability to signup, purchase, etc – any conversion event.

But when we went out into the market, only the largest companies were buying it.

JS: That doesn’t sound like a bad thing.

Lesson #2: Make sure the customer problem you are solving has a large market

BM: Well, it was great at first. Big companies were, and still are, paying us six figure contracts.

But selling to large companies has its disadvantages as a startup. The sales cycle is slow. They engage infrequently. That makes the time to iterate on your product very slow.

As a startup, time and velocity are key. If you’re going to be enterprise-first, make sure you’re able to convince a VC to give you a boatload of cash upfront.

In our case, we realized that while our predictive audiences / scoring product was useful to some large companies, it was too advanced of a use case for most. But it took us a very long time to figure this out, given the slow sales cycle of enterprise sales.

JS: So how did you expand the market opportunity of your product?

BM: At first, we tried to re-sell our existing product to smaller companies. But that didn’t work either.

You can’t just re-sell the same product to two different customer verticals. Companies of different sizes have different needs, buying motions, even if they’re trying to solve the same problem.

Optimizely for instance shut off its self-serve plan because they realized their A/B testing product was more successful for companies with more traffic. They made the mistake of never building a new self-serve product, but that’s a topic for another time.

Lesson #3: Have a self-serve and enterprise products to increase your market potential and speed up learning

JS: So it sounds like having both a self-serve product and an enterprise product are important in your opinion.

BM: Yes. Look at the most successful companies in the last year. Slack, Stripe, Zoom. All had massively successful IPOs or multi-billion dollar businesses. And all of them have served both self-serve and enterprise customers.

Having a self-serve product enables you to learn faster from your customer, and know it can make money. And having an enterprise product enables you to make the actual money. Even if 80% of your revenue comes from 20% of the customers, the bottom 20% can grow into your top 80%.

JS: So we should just copy Slack and Stripe’s playbooks?

BM: Well, another thing interesting about each of these companies is that their underlying products were themselves not new. Slack is a better HipChat. Stripe a better Paypal. Zoom a better Webex.

That struck a new insight for me that most of the new wave of successful startups (in SaaS at least) aren’t inventing something wholly new, but simply re-inventing an existing product with at least one differentiated value prop. It also does all the research for you that that product has enough of a large market.

Lesson #4: Really successful startups often look like existing products—just with one major tweak or update

JS: How did you take that lesson forward with ClearBrain?

BM: I assessed what are the existing billion dollar products that already exist out there in analytics. Adobe Analytics, Google Analytics.

It was already clear that those were multi-billion products with an identified market, customer problem. So rather than try to build a single feature of that product experience (i.e. predictive audiences), I decided to rebuild the whole platform.

JS: What was your differentiation though?

I thought back to why I started ClearBrain again in the first place. It was because the traditional analytics tools I was trying to use could not answer the question of “Why” – namely the problem of causation vs correlation.

It was clearly such a hard problem that no one else had solved it. But the hard thing is what would make it both differentiated and defensible.

Lesson #5: Solving for the harder problem gives you differentiation and defensibility

JS: But you said before you didn’t know how to solve the problem of causation vs correlation?

BM: Yep, and I still didn’t.

But that was another important lesson I learned as a founder. My job wasn’t always to come up with solutions. It was to identify problems. And enable (and listen) to my team’s solutions.

The solution to solving the problem of predicting causation in turn came from one of our engineers. She had looked up older statistical techniques that had been used in the medical field to predict treatment effects. She proactively assembled a lunch & learn, and taught us about concepts like propensity score matching. My cofounder in turn recognized they had applied similar techniques while at Google Ads, but at a larger scale.

It was a turning point in our company. We realized we could apply these old techniques, using our auto-ML technology we’d already built, to rebuild an analytics platform that could actually predict causation vs correlation.

Lesson #6: A founder’s job is to describe the problem, not necessarily the solution. Your team is often much smarter than you to actually solve the problem.

JS: So how does predicting the “Why” or causal effects actually work? Isn’t that part of the challenge of AI in general is that sometimes it’s not clear why it’s operating in a certain way? Like with AlphaGo (an AI that beat the world’s top human Go players), even the programmers weren’t always clear on why the program was acting in a certain way except that it increases the probability of a wins at the end.

BM: Exactly. Machines make decisions by taking all these different behaviors, analyzing correlations and manipulating things to get to one big right answer.

We needed a new algorithm that could use the statistical techniques our engineer had proposed, and apply them at scale in the manner Google Ads did.

But again, the benefit of being less top-down about the product direction and giving larger level objectives for what we’re trying to do, the team filled in the details on how to solve it.

Our ML engineer spent six months researching the problem and found ways to automate causal methodologies like observational studies at scale. We’re effectively simulating the effect of an A/B test on thousands of variables in seconds, to predict the causal effect of every page, button click, and action on your website. We go into more detail about the methodology on our blog.

JS: So if I understand it correctly, the result of your causal algorithm is you can rank the most important insights on a website by their causal effect, rather than correlations.

BM: We like to say that what we’re doing now is actually kind of like Google PageRank for analytics.

PageRank helped Google deliver the best content to users based on the relevance of that content to their search queries. With Causal Analytics, you can enter a goal like signup or purchase, and we rank each behavior, ad campaign, email open on your website by its relevance to that goal. Relevance in the context of Google is determined by weight of links, while in ClearBrain it is determined by the simulated conversion lift.

JS: How do you actually know your results are causal and not correlated though?

BM: A couple ways.

In the background we run tests via synthetic data analysis. We create artificial data using gaussian models and randomly perturb the data to see if our causal projections can accurately predict the observed changes.

But in the end, the best proof our insights are causal are the results our customers see. Our customers have seen between 40%-100% lift in their conversions by productionizing the insights we recommend – which wouldn’t be possible if our insights were correlated.

Lesson #7: You know you’re on the right path when your customers tell you what they want, instead of you asking them what they want.

JS: How has the concept of causal analytics been received?

BM: Really well. It’s funny because a lot of times founders will ask how do you know if an idea has some semblance of product market fit. The unsatisfactory answer is often you know it when you see it.

In our case, after 3 different iterations over 3 years, we started to feel it last month when we launched Causal Analytics into an open beta. 1000s of users have signed up so far. They’re asking us to build specific features, instead of us trying to guess what they need. It’s a clear feeling.

JS: So to companies trying to create their own product category today, what’s the high level advice you’d give them.

BM: Amusingly, I’d give the same advice a lot of other founders gave me, but just took a long time to sink in. Namely:

  • Don’t build a technology, instead solve for a customer problem first.
  • Make sure that problem has a large enough market to sell into.
  • It’s easier to validate markets as a startup by releasing a self-serve product, as it increases your pace of learning.
  • But its also important to have a path to an enterprise offering which actually generates revenue.
  • Your self-serve and enterprise offerings should not necessarily be the same product.
  • The irony of creating a new product category, is that the most successful ones are just evolutions of an existing category.
  • Copying an existing company leapfrogs a lot of the need for market research and validation.
  • It’s important to still have a single differentiated wedge to stand apart from the competition.
  • That differentiation can come from solving a really hard problem. Always solve the harder problem.
  • Your job as a founder is to identify problems, not solutions. Your team is better at that.

What We Should Learn from the Away Scandal

A debate about tech workplace culture in the era of Slack, #metoo, and self-care

The spectacular fallout from a recent investigation into Away, which portrayed the beloved luggage company as a toxic workplace, has revealed two schools of thought on how to treat startup employees.

The first says that staff should be cherished, because harnessing the passion and brilliance of “A players” is key to success. Think catered lunches, beautiful offices, and “Best Places to Work” lists. The second says that making a dent in the universe is hard, and employees should expect to work tirelessly under the directives of visionary and sometimes mercurial founders. Think “hustle culture,” Class B voting shares, and Steve Jobs’ infamous tirades.

These ideas are not mutually exclusive, and the truth is most companies operate on a bit of both. Away was no exception.

Over the past four years, the NYC-based luggage brand achieved cult status in the travel category. Founders Steph Korey and Jen Rubio raised $181 million in venture capital over five financings, blanketing the city’s subways with ads for their colorful rolling hard-shell suitcases with built-in chargers, and largely positive press coverage from NYTimesTravel + Leisure, and other outlets.

But last Thursday, The Verge published an article about Away, now valued at $1.4 billion, that started a rousing online conversation between tech investors, founders, and operators about how far Korey went to make Away a success. In the piece, 14 former employees described a culture of surveillance, verbal abuse, and an exhausting workload that spanned late nights and weekends with restricted PTO. Four days later, the company announced that Korey would be replaced as CEO by Stuart Haselden, currently COO of Lululemon. (Korey will become executive chairman.)

Having been both a founder and an employee of multiple tech startups, I understand this is a complicated issue. Founders are under enormous pressure to deliver results to their investors and that pressure can manifest in all sorts of ways to employees. The story of Away has become something of a Rorschach test for Tech Twitter as these two schools of thought come into sharp contrast.

Some felt the criticism of the company was unfair. LA investor Peter Pham called the article a “hit piece” and said “people are getting soft,” while Lambda School founder Austen Allred argued that “something like 99%” of all high-growth startups could have a similarly negative piece should a reporter go looking for it. 

Some pointed out that many of the complaints in The Verge’s story came from Away’s customer experience (CX) team, a particularly critical department for e-commerce companies. Management expert Melissa Nightingale believes CX is “the lifeblood of our orgs” but is often ignored and told to stop complaining. “We burn them [CX] out and we totally know it,” the former Mozilla executive said in a series of tweets.

While many held Korey responsible for the problematic culture, others also noted that the bigger issue may be investors.

Erica Baker, a group engineering manager at Microsoft, expressed frustration at VCs who seem willing to “overlook/champion psychological abuse” in the name of making the business successful.

Given how quickly Away named a replacement for Korey, it seems the company’s investors, which include Forerunner Ventures, Global Founders Capital, Comcast Ventures, and Wellington Management Company LLP, may have been aware of her alleged behavior and were working behind the scenes to change up leadership.

Here’s what I think: The definition of an acceptable work environment is changing. What might have been considered normal 30 years ago, such as casual sexism, racism, ableism, have become far more scrutinized—and that’s a good thing. Tech employees should expect to work somewhere free of verbal abuse, emotional manipulation, or extended unpaid overtime.

And yet we know that big funding rounds, intense founders, and scaling problems are breeding grounds for toxic workplaces, and none of those things are going away any time soon. So what do we do as an industry?

First, recognize the dangers of over emphasizing short-term results. Brian Wang, an executive coach who has been a founder (Fitocracy) and operator (Credit Karma, Eaze) has seen this first hand. “Long hours or surveillance culture can, in a vacuum, lead to more productivity by some measure,” Wang told me over the phone. “But it fails to take into account trade-offs like employee longevity, organizational trust, and willingness to share information.” Startups are a marathon, not a 100-meter dash, and operating at a sustainable pace is critical. As I’ve argued before, working long hours is unhealthy and a poor way to drive long-term results.

Second, understand that bullying is harmful and contagious. Research at the University of New Hampshire has shown that ridicule, public criticism, and silent treatment has negative effects not only on those targeted but on those who witness it. I once saw the cofounder of a company teardown our social media manager in a marketing team meeting for a minor issue. Productivity was shot for the rest of the day. In the case of Away, their Slack policy of public rooms meant that anyone’s angry missives would be highly visible. Not only that, but witnesses of bullying are more likely to bully themselves, so the abuse spreads, increasing everyone’s stress levels and preventing people from working at their best.

Third, help founders and employees alike find safe places to share fears and ask for help. Rubio and Korey saw the value of confiding in one another at a previous firm but punished employees who tried to create such a space for themselves. “I think even just acknowledging the fear that is there can loosen the grip that so often drives that anxious behavior,” Wang says. And while lower-level employees do have to be more careful about who they confide in, finding allies and cultivating relationships when you know you can’t immediately jump ship is really critical as well. In a silver lining, some of the best work relationships are formed in the crucible of misery, whether that’s a bad boss or a project gone sideways.

Ultimately, Away might have been a victim of its own success. The Verge article closes with a quote from Away’s former marketing manager: “Never work for your dream brand. It’ll kill you.”

The company was so beloved and expectations so high that employees were inevitably let down when they experienced a work culture that felt more like law, finance, or advertising, industries known to be grueling. As anyone who’s ever had a bad vacation knows, paradise is almost never what it’s cracked up to be.

This first appeared as a contributed piece in Fast Company

Why Generalists Beat Hyper Specialists

Book notes on “Range” by David Epstein

I’ve always seen myself as someone with a ton of interests, with a lot of useful skills and knowledge but not a world class expert in anything. And while that’s served me really well, I sometimes wonder if it puts me at a disadvantage.

Fortunately for me, I recently finished Range: Why Generalists Triumph in a Specialized World, a thoughtful and comprehensive read by David Epstein. It made the rounds on VC Twitter this summer, which makes sense because venture capitalists, especially early stage ones, are very much generalists who look across a broad set of industries.

I recommend reading this alongside Peak: The New Science of Expertise — you can see my interview with the author, Erik Anders.

Here are a couple of my favorite ideas and passages. Anything in quotes is from Range unless otherwise indicated.

Tiger Woods vs Roger Federer

Epstein previously wrote a book on the science of athletic performance and has debated Malcolm Gladwell on what they call the Tiger vs Federer model.

Tiger Woods was famously playing golf and winning tournaments at a very young age, trained by his father. He was a prodigy and was dominant in the sport until overuse injuries and a bit of mental and marital breakdown took him out for some time—though he’s making a bit of a comeback now.

Roger was apparently playing a bunch of different sports including soccer into his early teens before deciding to really focus on tennis. He’s seen as one of the most dominant tennis players of a generation and at 37, which is old for tennis, still winning titles.

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Community is just friendship

WeWork, well-being, and who we are

Working in tech, you hear the word “community” a lot. When I was starting my career more than a decade ago, the concept of a community manager was starting to go mainstream.

Today it forms the foundation of our industry’s latest IPO – WeWork. For years they have been crowing about the power of community.

From their mission page:

When we started WeWork in 2010, we wanted to build more than beautiful, shared office spaces. We wanted to build a community. A place you join as an individual, ‘me’, but where you become part of a greater ‘we’. A place where we’re redefining success measured by personal fulfillment, not just the bottom line. Community is our catalyst.

The truth is, this language is more hype than reality. People sometimes becomes friends at WeWork, and sometimes they’re just deskmates who never talk. The core thing that unites these people is the need for work space, which is not a very strong place to start.

This is not a takedown of WeWork. Plenty of folks have done that better than I, including Scott Galloway (WeWTF) and Harvard Business Review (No, WeWork isn’t a tech company)

I will say however that WeWork’s infamous Summer Camp is where I’ve cemented a number of friendships. One in particular was someone I had met a few times but finally decided to invest in a deeper relationship with. And for that I am grateful.

I’ve been thinking a lot about community.

Perhaps because I’m living in Seattle for Techstars Alexa, away from my wife, my friends in New York. I’m stepping into some new communities: of my fellow founders from this batch, the folks living in the Seattle area, and the Techstars community at large. I’m also trying to build a user community for my business, Midgame.

In The Art of Community, Charles Vogl defines the term to simply mean a group of individuals who share a mutual concern for one another’s welfare.

It’s not about shared interests, shared activities, or even shared beliefs. Although those things often happen in communities, what defines them is that the participates care about each other’s well-being.

That sounds a lot like friendship.

Creating community means encouraging friendship. When an old classmate invites me to dinner, that’s community. When I call my friend who became a parent and a startup founder in the same month, that’s community. When I introduce two people to each other who I think will get along, that’s community.

Vogl goes on to say how strong communities tend to have certain qualities:

  • Membership identity (Who am I?)
  • Shared values (How should I act, what do I believe)
  • Moral proscriptions (What do I uphold? What do I abhor? How do I show respect?)
  • Insider understanding (What do we all understand about the world?)

Think about the communities you are a part of. Friend circles. Alumni networks. Families. Activity groups. Work mates.

Each of these communities answers these questions. The stronger communities do so more clearly and powerfully than others. This is the stuff we often think about and talk about when we discuss community management, along with rituals, tokens, invitations, hierarchy, and other topics in the book (if you can’t tell, I think this book is great).

I think of my communities of startup founders, folks in NYC, former gymnasts, Stanford alums, civic techies, Asian American men, my family, even my mutuals on Twitter. They profoundly shape what I think is funny, or important, or harmful and how I behave. Which means I should be mindful of which I invest in, since they make up such a big part of I am, who we all are.

But at its core, a community needs to share mutual concern for each others welfare. I write in part to serve my readers. So if you’re reading this and you care about me even a little bit, then we’re at least a 2 person community, even if we never meet or communicate.

We are living in an epidemic of loneliness and easy targets like “social media” don’t address the complexity of the situation. Joining or creating communities both online and offline can help address that.

Techstars Alexa

Midgame joins Amazon’s voice-focused startup accelerator

Midgame was accepted into The Alexa Accelerator, a program co-run by the Techstars startup accelerator and the Alexa Fund, a $200M fund for Amazon to invest in voice tech companies. We’re two weeks in and over the next few months, we’ll build and launch a voice assistant for gamers, alongside nine other companies who are also part of the program.

The announcement went live on VentureBeat last week as well as the Amazon Day One corporate blog.

The other companies in the program include include an AI-powered service that helps students learn, a health product that checks up on patients between visits, and a tool for quickly taking notes when listening to podcasts. They’ve collected an impressive group out of the hundreds of applicants and many of the founders are on their second or third company.

The program is run out of a coworking space near the University of Washington campus so I’ve temporarily relocated to Seattle through the fall. If you’re in the area, I’d love to say hi.

Long-time readers know I went through Y Combinator in Summer of 2011, when there were only 63 companies and Paul Graham still ran the program. It’s obviously changed a lot since then. I’m interested to see how Techstars compares. One difference that’s widely stated is that Techstars is more structured and has more of a “curriculum” compared to YC. A conference vs Burning Man if you will.

For instance, Techstars does something early on called “Mentor Madness”. Two weeks of back-to-back meetings where we sit down with 50+ people, founders, venture capitalists, engineering leaders, BD folks, lawyers, and more to rapidly pitch our idea and get a wide range of perspectives.

As one Techstars founder put it:

One of the great innovations of Techstars Accelerators is the aptly named Mentor Madness. It’s a grueling and emotional exercise that presses everyone to the limit. The politest description I can offer is that it feels a bit like having Christmas and a root canal at the same time. You’re excited about unwrapping presents, but horrified about a stranger digging holes in your head 😀

I was skeptical of the approach at first but it’s a great way to rapidly iterate on your pitch to see what points stick and learn about companies and people in your space. I also expect we’ll have some new thoughts after next week is over and we can really digest all the feedback.

Mostly though I came out of the meetings feeling like we’re headed in a good direction and while we have lots of work to do, if we keep digging, we’re bound to hit something really interesting.

That said, we’re looking for people who play a very popular indie game called Stardew Valley to test our first voice assistant. If you or someone you know plays, we’d love share what we’re working on: http://www.midgame.gg/stardew

If you want really help out, drop that link into your company’s #gaming or #games Slack channel if there is one and you could help us get the word out.

Conflict Isn’t Always Bad

My natural tendency is to avoid conflict. The few times I fought in school, I was caught and punished for it and it didn’t seem never was worth the trouble.

It’s also the case that needless conflict can be harmful to both parties, because even if you “beat” the other party, now they’re holding a grudge.

But I’ve come to realize the value of productive conflict.

Sometimes it’s better to get to the root of a disagreement right away so you can understand it, hash it out, and resolve it. This of course requires you to disagree without getting into personal attacks (of course you’d say that you coward), and the issue at hand needs to be important (business direction vs business cards).

There are frameworks for productive disagreements, one of the most popular is non-violent communication. Another similar one I discovered recently is called The Feedback as described in The New Rules of Marriage. Being a co-founder or closely working business partner is in many ways mirrors a marriage.

This process starts by having you ask if your partner if they’re willing to listen. Once they’ve confirmed, you share with them:

  1. What you saw or heard that you found problematic (I saw you come into the meeting 20 mins late)
  2. What story you made up about it (this is where things usually go off the rails, focus on your interpretation – the story I made up was that you don’t care about the team)
  3. How you feel about it (it made me feel like I have to carry this project on my own)
  4. How you’d prefer it go down next time (give me a heads up next time you’re going to be more than 10 mins or reschedule the meeting)
  5. Let go of the outcome (also not easy)

Hashing out smaller conflicts sometimes stave off bigger ones.

Seth Godin calls this “thrashing early“. It may not always feel comfortable in the moment, but it makes things a lot easier later on. By putting your foot down early on, it prevents bigger blow ups or larger scale fights down the road.