Hayden Williams

Hayden Williams

Co-founder of Treatings

In praise of constraints in building a startup

Building a startup is daunting, an exercise in organization, prioritization, and execution. An endless number of tasks calls for a founder’s attention, none of which can be derived from a cookie-cutter blueprint. Believe me, I’ve looked.

So, how do my co-founder Paul and I work through the significant tasks that jump to the top of ourTreatings to-do list? I’m talking about the vital items, those even more important than getting organic cotton t-shirts embroidered with our ever-changing logo and launching ice-cold emails asking Nick Bilton to write about us. (I don’t care what anyone says. “Hatching Treatings” is a concept for a story, opening with Paul and me in the middle of a high-stakes power struggle: whose turn it is to sleep in the top bunk.)

Our tool of choice in figuring out how the hell we’re supposed to build a startup: constraints.

Like any green entrepreneur, when I quit my investment banking job to start Treatings I wanted the product to have the broadest appeal. I figured, who wouldn’t benefit from a professional networking platform that facilitates one-on-one meetups over coffee? Instead of making the mistake of limiting ourselves to one demographic, let’s welcome everyone.

I’ll wait for the grizzled startup veteran’s eyes to complete their 360 degree roll.

We’ve learned that constraints play an integral role in building a startup, from defining the community, designing the user experience to determining an appropriate workplace culture. We’re still searching for the appropriate balance of imposing constraints without being oppressive, but here are some things we’ve learned.

Community definition

When we started, I agonized over every website copy change, fearing we’d alienate a potential user base. Paul and I have had countless conversations around whether we should explicitly say that Treatings is a networking platform for “young” professionals.

We’ve found that before defining what our community is, we need to be unequivocal about what it isn’t. We facilitate professional interactions; we aren’t a dating site. The goal is to facilitate mutually beneficial peer-to-peer conversations; we aren’t an expert network. The goal is for conversations to be taken offline; we aren’t a messaging app. Each artificial constraint reduces our market, which is actually good. It gets us closer to having a definable group of users.

Marketing to a specific demographic is the first challenge. Getting our target market to engage with the platform comes next. We need to overtly define our community’s reason for existence for the same reason dating sites need to. To propose a date with a stranger, you need to have comfort that everyone on the site is open to meeting new people.

I don’t think anyone would send a message to a stranger on Facebook saying “How about we put my archery license to good use and head over to an archery range.” That would be reason to alert the authorities. But that’s a real date proposal on the dating site How About We. It’s all about context.

If you’re going to reach out to a stranger, whether to ask them on a date or ask about their work, you want to know that everyone has opted into the platform for this singular purpose.

User Experience Design

I’m not an accomplished UX designer, which is why I’ve had to learn a lot of lessons the hard way. I was surprised to find that the more structured we made our framework, imposing artificial boundaries, the more engagement we saw.

In “The Design of Everyday Things,” author Donald Norman writes that when designing a product, “constraints are powerful clues, limiting the set of possible actions. The thoughtful use of constraints in design lets people readily determine the proper course of action, even in a novel situation.”

There’s uncertainty involved in asking a stranger out for coffee. In order to feel comfortable proposing a meeting on Treatings, individuals need to know that fellow members are expecting such requests. In the past we’ve considered lessening our emphasis on in-person meetings and just being the best way to contact professionals outside your network. In speaking with members, we found this would diminish their likelihood to engage since there would be less clarity on why fellow members were on the platform.

After making it clear that everyone in the community is open to meeting, we must provide social proof that others are utilizing the platform. This an area where online alumni networks fall down. While most alumni directories have a healthy supply of individuals open to sharing their insights, they are essentially static directories, which isn’t a good environment to spark conversation.

There is a danger of imposing too many constraints. In past iterations we mandated that when reaching out to someone for the first time you had to propose a place/time to meet. We reasoned that if we made it clear that these were the rules by which everyone abided then people would overcome their anxiety from appearing too forward. We found this was too restrictive and stopped some users from sending introductory messages.

Workplace Culture

I’m not an authority on creating an awesome workplace environment, given we’re a bootstrapped team of two. Our biggest focus is on not adopting the “culture” of our work environment, New York University’s Bobst Library, which is essentially a dormitory for stressed out students.

I do have first-hand experience on how not to create a healthy culture. In my prior job in finance there were way too many constraints: artificial deadlines passed down the ranks with little notice or reason, deliverables had to be done within the confines of pre-approved templates and face time was celebrated.

In the startup community, I have observed an appropriate balance between creating constraints and giving employees the flexibility to operate within them. The happiest employees I’ve spoken with work in a structured environment where success is clearly defined and goals are set. But, they are given flexibility to operate within that framework, evaluated based on execution and performance above all else.

According to my “research,” people’s appreciation of constraints doesn’t apply to employer-provided free food, beer and house cleaning.

This post was originally published on PandoDaily.

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Our marketplace is growing… too soon?

When we opened the beta of our local professional networking platform, Treatings, in New York City last summer, we didn’t have a specific timeline for when to open it more broadly. We wanted to run experiments to determine the best framework for facilitating one-on-one meetups over coffee.

We figured NYC would make for a nice laboratory, although there wasn’t much premeditation to starting the company in New York. My co-founder Paul and I had quit our corporate jobs and builtbunk beds in the room we shared, so we had established roots in NYC.

One problem with keeping our beta restricted until finding the best framework is that “best” is nebulous. I’m not sure we could ever say we found the best way to connect people, just better or worse than previous iterations. In truth, we’ve found comfort operating beneath the “NYC beta” umbrella. We’ve deflected questions about our user growth by pointing out that “Well, it’s a closed beta. We’ve wanted to iron out the product before shifting focus to user growth.”

Constraining our beta to New York has been like slapping a governor on a car. We’ve implemented this speed limiter to create the perfect environment for controlled testing and tweaking of our platform. We actually haven’t wanted runaway growth!

Well, maybe we wouldn’t mind runaway growth.

The reality is that many of the experiments we’ve been running require a certain amount of liquidity to prove meaningful results. We’ve facilitated hundreds of coffee meetings in New York, but that needs to be thousands. We’ve embraced Paul Graham’s notion of Do Things that Don’t Scale, signing strangers up in coffee shops, manually facilitating connections and taking our users out to coffee in order to get feedback. We’ve had engagement, but need to prove that it’s sustainable without our heavy hand.

When I’ve asked entrepreneurs who have experience building and scaling marketplaces when to expand to other markets, I’ve heard conflicting views. In one conversation, I was nodding my head as the entrepreneur explained that “You should never grow to another market until you’ve built one self-sustaining community.” No sooner am I embracing the focus-on-one-market strategy that I hear “What’s the barrier to you rolling out in SF? Are you actually partnering with coffee shops to set up the meetings? Doesn’t feel like you need to do a local market rollout go-to-market like an operationally-intensive business like TaskRabbit has to do.”

Since we’ve accumulated signups outside of New York City, I’ve also heard contradictory views from users on whether restricting our beta for seven months was a good or bad idea.

You can guess what camp this person was in, emailing me that “To be told I cannot use your service because you’re currently in NY only is a lost opportunity when I could still be communicating with people of interest… That’s just limiting your business.”

I appreciated that feedback, but had to reconcile that with notes like this one: “Just go slow and nail it, then get the cash and expand. NYC is a great place to start.”

New York has been a good environment to experiment with Treatings because of the breadth of industries represented here. Before we started coding, we spent time approaching strangers in our target market, asking how they meet professionals outside their network. The unsurprising answer was that people didn’t have a problem leveraging their network to meet people in their industry. But, if looking to learn about new skills, find collaborators or explore career opportunities outside their industry, their preexisting network was less helpful. For that reason, we decided that Treatings would be industry agnostic from day one.

Where better to build a platform that requires representation of many industries than NYC, a city that has an investment bank, two fashion brands, three startups and four frozen yogurt shops on the average block. If we had started Treatings in San Francisco, where people are predisposed to being early adopters of technologies, we would have run the risk of building a framework non-transferrable to other cities. We’ve found our largest barriers to be social-based, as opposed to technological, as we seek to create an environment where people feel comfortable proposing meetings with strangers. While I don’t have empirical data to support this, I think we would have found the social barriers to be lower, and therefore not representative of the average city, in San Francisco.

Don’t get me wrong, New York has its own nuances. There’s a crazy person peeing on my leg as I type.

What began as seeming like a decrease in work, limiting ourselves to one city, turned into a headache. It’s taken time to maintain the geo-fences that keep everyone but residents of NYC out of Treatings. Our focus on improving our NYC beta has been to the detriment of the user experience for users outside NYC. They have been unceremoniously signed out after creating a user profile.

So, with all this in mind, we’ve decided to open Treatings to everyone. I’m hoping that users who previously signed up from outside New York, for whom we didn’t design a proper experience the first go-around are willing to give Treatings a second try as we continue to mold our product. Our product is far from complete. We haven’t found that elusive “best” framework to connect people, but we have learned a lot.

We’ve learned that people need to see activity on the site to feel comfortable engaging. We’ve learned that we can’t make users do work up front before providing any value (This is one of many things we were warned about but had to learn first-hand.) We’ve learned that underlying our innumerable design flaws, people still appreciate a good conversation with a side of caffeine.

With the benefit of hindsight, we’ll be able to look back on our NYC beta and judge whether we kept it restricted for too short or too long. For the record, Paul has been in favor of opening everywhere sooner rather than later, while I’ve been more reserved. I’m just looking forward to the healthy process of one of us hand-delivering “I told you so’s” to the other.

This post was originally published on PandoDaily.

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Should our startup join an accelerator?

A few months ago I was catching up with my mentor, an experienced entrepreneur. I love getting together with other founders, especially those a few years ahead of me. It’s not unusual for me to walk away from such meetings convinced we should try something completely new with our startup, or reverse a previous decision. You’d have to ask my co-founder/CTO Paul which is more annoying.

This conversation was no different.

He asked how things were going with Treatings. I paused, reflecting in order to give him an honest answer. “Everything’s great!”

Remember that time I wrote that I was determined not togive the toothy “everything’s perfect” grin when asked about Treatings? I’m still working on that.

Anyway, I told him that we’ve been growing the user base of our local professional networking platform. Apparently startups aren’t supposed to operate like nonprofits forever, so I went on to tell him about how we’re testing our business model. Specifically, approaching employers in New York about having a Company Page on Treatings.

His first question was, “How are you finding customers?”

I proudly explained that often we’re referred into companies through employees already using Treatings. Underwhelmed, he noted the scalability challenges of reaching out to individuals on our site and hoping they can refer us to the proper person in their company. “Are you applying to any accelerators?”

“No, we’re not.”

“Why not?”

I mumbled that we wanted to be laser-focused on our product and business model. He’s a mentor for a local accelerator and believes that a top-tier accelerator would be invaluable at our stage. He highlighted how accelerators would be able to make introductions into the same venture-backed companies, those with hiring needs and cultures they’d like to showcase, we are seeking to help.

Despite that we had ruled out applying to an accelerator, I ran back to Paul thinking we should. As we thought through the merits of applying, here are some of our explicit and implicit reluctances:

Reject me six times, shame on you. Reject me seven times, shame on me.

One primitive reason why I had written off accelerators programs was a “we’ll show them” attitude. In the early months of Treatings, we sent a total of six applications to various accelerators. We got rejected from all of them. Our product was not in a great place for any of the applications. But, at least for the last few, we felt like we did an effective job of explaining what we envisioned for Treatings. We took the rejections as just as much a comment on our vision as our crappy prototype, and so were resolved to go it alone.

We’re no Martin Scorsese.

All of the accelerator applications we’ve filled out have required at least one video submission, introducing the team and product. One word for these videos: awkward. For starters, we have no good place to film them. The 10 x 12 bedroom we share doesn’t paint a picture of organization, maturity or a mind for design, all qualities I imagine are important in evaluating startup teams. Our bunk bed dwarfs the space and there’s a tornado of feathers, which spew from our comforters, spilling over the twin XL bed frames. The room screams snow-globe chic.

Our “office,” AKA New York University’s Bobst Library, has had to make do as our backdrop for self-documentary. What this looks like is Paul and me sitting on the floor, shoulder-to-shoulder in the hallway, holding an iPhone in front of us. You’d have to ask the students what they think is going on as they step over the extended legs of two guys clearly not undergrads, filming themselves talking about how long they’ve known each other and blabbering about something called Treatings.

The video on it’s own isn’t a barrier to applying to these accelerators, but it’s not a pleasant proposition.

Bubble Boy

A look at my employment history reveals someone with a poor sense of timing. I sold knives door-to-door in 2004, missing the boom of door-to-door sales by a handful of decades. My foray into real estate was closer to the peak, as I bought and renovated a foreclosed property in 2005. Housing prices were peaking as we put the house back on the market and we were fortunate to get out as prices were plummeting. From there, the logical next step was to join an investment bank in June 2008, two months before Lehman Brothers went bankrupt. After riding that wave, I co-founded a tech startup in 2012.

I don’t have the perspective to weigh in on whether there’s a “startup bubble,” or even what that means. But, I am wary of jumping to the next hot, or even worse, cooling, thing. It’s not hard to find articles denouncing accelerators and their impact on the startup community, although these are typically not aimed at “top-tier” programs.

Getting pulled in multiple directions

I’d say the most rational hesitation we’ve had to reapplying to an accelerator is the risk of getting pulled away from our product. I’ve spoken with alumni of reputable accelerators and if there is a complaint, it is from startups who entered programs at a stage when they were scaling and/or monetizing. They said it could be difficult maintaining product focus when there’s a revolving door of incredible mentors stopping by to drop off their two cents.

Mentorship is our greatest attraction to accelerators. Paul and I have always been intent on making original mistakes. What better way to avoid repeating other’s mistakes than to expose ourselves to the pool of peers, alumni and mentors associated with the best accelerators. We’ve just been trying to reconcile the immediate benefit of immersing ourselves in our product and user base with the long-term benefit of learning from people who have built and scaled successful businesses.

We decided we will test out the accelerator waters once more, armed with my blind optimism, which promises to rationalize the outcome, no matter what happens.

This post was originally published on PandoDaily.

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What, me worry? How blind optimism benefits startup founders

Building a startup is an emotional roller coaster. Look no further than Paul Graham’s startup curve. If you take as a given the parabolic trajectory, how does a founder handle the ups and more importantly the downs? I’ve developed a systematic strategy that has worked wonders in keeping me upbeat. What’s more, I’ve stumbled across research that shows I might not be (altogether) delusional.

So, what’s my “scientific” approach? When Treatings has successes, no matter how trivial, I heap credit on my co-founder Paul and me, and hang on to that positive feeling for as long as possible. In the more common occurrence that we face setbacks, I instinctively deflect it as insignificant and temporary. An external force outside my control that is best forgotten.

I’ve become frighteningly adept at this. It’s not even a case of bottling up negative emotions that are apt to erupt from time to time. A dose of justification, combined with a short-term memory, remedies most adversities.

An investor we meet at a networking event doesn’t think Treatings, a professional networking platform where you can offer to treat strangers to coffee, is a viable business? That’s easily shrugged off because people who give away money for a living aren’t going to want a way to be asked out for coffee. They’re already drowning in such requests. If we had more time to frame the fact that Treatings is aimed at surfacing insights from peers, not connecting with public figures, surely the investor would be won over.

What about when a customer pitch ends in a “no?” Surely this crushes my spirits and sends me spiraling into a pit of despair. Are you kidding? Do you know how many times restaurant owners said no Colonel Sanders when he was hawking his fried chicken recipe? 1,009 times! Seems to have worked out pretty well for him, and I happen to love his product. I could use another notch in my “no” belt anyways.

I’m not oblivious to my optimistic, as I’ll charitably term it, nature. Every day we’re faced with the same rejection and criticism all founders can relate to. I don’t give myself Richard Simmons-esque pep talks to stay positive (except for Tuesday morning spin class). I just reflexively process and discard negative news, while soaking up the victories. Like any true delusional optimist, I’ve stumbled into research that has (in my mind) reaffirmed my behavior.

In “To Sell Is Human,” Dan Pink writes that although only one in nine Americans work in traditional sales roles, we all spend our day selling, whether entrepreneurs pitching investors or parents convincing children to go to bed. He explains that an essential quality in effective salespeople is “buoyancy.” This is the ability to keep your head above water amidst the sea of rejection most of us face on a daily basis, whether it’s investors dismissing your product (hypothetically of course) or your kids refusing to go to bed.

One of the main determinants of buoyancy is your explanatory style, which is what you tell yourself after an experience. What’s an easy way to drown? Have a pessimistic explanatory style – “the habit of believing that ‘it’s my fault, it’s going to last forever, and it’s going to undermine everything I do.’ [This] can diminish performance, trigger depression and turn setbacks into disasters.”

To be buoyant, to bounce back after rejection, Pink advocates an optimistic explanatory style. This is described as the tendency to “see rejections as temporary rather than permanent, specific rather than universal, and external rather than personal.” Not only does a positive explanatory style lead to a sunnier disposition, it apparently leads to more success.

Pink quotes a study conducted by researchers at the University of Pennsylvania, where they studied approximately 100 sales agents from the Metropolitan Life Insurance Company. The researchers completed a psychological assessment to determine the explanatory style of the agents, then tracked their performance over two years, measuring total sales and commissions earned. The results showed that “agents who scored in the optimistic half of the explanatory style sold 37 percent more insurance than agents scoring in the pessimistic half [and] agents in the most pessimistic half ended up quitting at twice the rate of those in the optimistic half.”

Turns out that buoyancy is a fantastic quality to have. Before my hand gets too sore from patting myself on the back, though, what’s the danger of such blissful buoyancy? The nice thing about the characterization is that you can never be too buoyant. That just means you’re a deity and can walk on water.

One thing I worry about is that I’m prone to blind optimism. I shouldn’t brush off all negative signals. Optimism and persistence are celebrated qualities in entrepreneurs. We’re supposed to run through walls and any obstacles that present themselves, in order to bring our vision to fruition. But what if those walls are telling us something we should listen to and let impact our trajectory? We must be headstrong and persistent while also acknowledging the difference between a hurdle and a dead end.

Unfortunately, there isn’t a right answer. It’s a tightrope that must be walked, tempering optimism with realism — a tight-rope I’m confident I’ll never fall off of.

This post was originally published on PandoDaily.

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Should a non-technical founder hedge against failure?

Recently I grabbed coffee with a founder whose startup is in a similar stage to mine. I reached out to him after he signed up for our networking platform. Because he had also started his career in finance I was interested to speak with him.

We shared the challenges we were dealing with, our product roadmap and plans to monetize our products. Towards the end of our conversation, we veered into the personal dilemmas early-stage founders face. He asked me, “What’s your plan if, worst case scenario, Treatings fails? Would you go back to finance, start another company or join an existing startup?”

It didn’t take me long to say what I wouldn’t do, namely return to finance. But I had a less clear answer on what I would do. It’s not something I’ve spent much time pondering. While I don’t know what I’d do, I told him, I wouldn’t have a fundamental objection to joining someone else’s company. He then gave me the following piece of advice: develop some expertise. “Startup CEOs don’t make for great employees,” he said. “While we get exposure to every part of running a business that doesn’t necessarily translate into marketable skills.”

I thought about it and realized how right he was. I’ve loved experiencing all aspects of building a product and company. I’ve learned about product development, UX/UI design, copywriting and even picked up a bit of front-end coding. But, I’m not so experienced in any one of those areas that I’d be a desirable candidate for a specialized role at an established company.

This brings up the question: should a non-technical founder hedge against failure? Our goal with Treatings is to hit an inflection point before running out of money. But, even if we shut down tomorrow I wouldn’t have enough money in the bank to sit on my thumbs for months to figure out my next step. After bootstrapping Treatings for the last year, I’ll eventually need an income. The plan is to generate money from employer-branded Treatings pages that feature employees offering to get coffee with outsiders interested in working at the company.

No matter how confident I am that we have created a valuable tool to monetize Treatings, am I supposed to be thinking about a contingency plan just in case we’re proved wrong?

This predicament is unique to a non-technical founder. My co-founder Paul tackled the challenge of stepping into the role of CTO, despite having never developed a web application. He bolstered skills picked up in his academic and professional background in computer science to build our site. Through grit and sheer man-hours, he has developed a skill set that every tech company in New York is desperate to throw six-figure salaries and kegerators at.

As for me, though, I doubt many are rifling through LinkedIn for people who occasionally blog (about their bunk bed), know a little front-end code (can change button colors sometimes) and have experimented with copywriting (know every synonym for “networking” in the English language).

Of course, some startup CEOs come into the role with expertise that would make them marketable in a variety of specialized roles within a startup. But, for non-technical startup founders who came from a different industry, I think in many ways the role of startup CEO on a small team (two, in our case) is conducive to becoming a jack of all trades, master of none.

For this reason, the founder I spoke with dedicates an hour a day to front-end code so he can become more technical. One of the advantages of this habit is that the same skill that would make him more marketable in the event of his startup failing also makes him more productive in his current role.

Unlike him, though, I don’t have any kind of backup plan. In fact, all I’ve done is rule out leaning on the most profitable skill I have (willingness to bask in the glow of Excel and PowerPoint, creating bank merger models for an amount of time out of my control). At this point, I don’t feel the need for a backup plan. It’s not because I think having a hedge is a sign of weakness, and it’s not because I think Treatings is fail-safe.

I’d like to think that the marketable expertise I’m learning is the holistic skill of how to build a company. There are legal, product, business and team decisions that must be prioritized and dealt with. Most of what I’m learning is through trial and error, but I’m learning just the same.

Is this skill transferrable outside of starting your own company? Maybe it’s time to think outside the box.

With all the time I’ve spent in coffee shops over the last year, perhaps I could become a barista. Given Treatings is all about treating strangers to coffee, we’ve been able to conduct many customer interviews and other meetings in coffee shops, concealing the fact we have no office and a caffeine dependency. The problem with that, though, is I’ve never ordered off the country club menu (anything other than black/iced coffee). I wouldn’t know how to make a grande decaf no whip soy Frappucino. More importantly, I’m follicly challenged in the moustache department so wouldn’t even look the part.

With my bunk bed familiarity, perhaps I could brand myself as a feng shui expert for dormitories, summer camps and hostels. Kids and travelers have phones they need to protect and pillows they don’t want to lose from the devastating two-story fall off of top bunk. I’ve experimented with solutions for both. Paul and I have also MacGyvered some under-bunk bed clothing storage solutions that IKEA might be interested in.

Or, I could just embrace the grizzled, failed tech founder and troll around Meetups and other networking events, desperate to find others’ ideas to crap on. You know those people, whose eyes gleefully light up in conversation when they find a perceived weakness in your product or business strategy they can highlight.

There are just so many exciting options to choose from.

This post was originally published on PandoDaily.

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Don’t call me Mr. Nice Guy (even if I am)

This past week I was speaking with the founder of a startup that’s been around for roughly five years and raised tens of millions in venture capital. It had been about six months since we last spoke. I was regaling him with tales of Paul and my bunk bed, recent mistakes we’d made in hiring a freelancer and our imminent plans to re-engage companies to turn Treatings into one of those businesses that make money. All things readers of this series (Hi Mom!) are tired of hearing about. About five minutes into our conversation, he abruptly asked, “So, are you happy?”

“Yes, I am,” I said, then quickly caveated. “I mean of course we haven’t proved that Treatings is a viable business, and my lifestyle is transitory, but I’m enjoying the process and learning a ton.”

He replied, “Sounds like you have a great, easy-going attitude. I’m jealous. I’m always paranoid and can’t relax when there’s so much left for us to do.”

I found this exchange interesting, not because of what he said, but because of how I felt about it. I took his comment as a backhanded compliment, like, “Being easy-going is a nice trait to have, but not necessarily if you’re trying to build a world-changing business.”

I felt a bit defensive. I didn’t want him to think I’m Mr. Nice Guy, content despite the tenuous state of Treatings. Later I thought, is being patient and accepting of the startup journey so bad? Maybe I should have whacked him upside his head with my phone to show him how bad ass I can be.

No startup founder wants to say they’re satisfied with where their product is, and for good reason. There’s always more to do, and complacency kills companies. I have been embarrassed by just about every product iteration we’ve released, but I’m happy with our trajectory. Maybe a better word than “happy” is “at peace.” We’ve made innumerable mistakes that we hopefully won’t repeat, but we’ve learned from them. So, how to be even-keeled and reconcile impatience with the state of the product with acceptance of the disorderly journey of a first-time entrepreneur?

When Paul and I hit roadblocks with Treatings, which is every day, our first line of defense is looking outward to see what we can “borrow” from others. We’ve modeled our professional networking framework after online dating sites, the messaging is informed by text message interfaces and ourbusiness model is inspired by employee referral programs. That got me thinking, should I also model my behavior after successful startup founders?

I’ve found that many of the most celebrated entrepreneurs could be placed into one of two buckets: the paranoid and gladiators. Of course, many founders could be classified as both. While the paranoid are primarily driven by trying to stay ahead of potential threats, gladiators are chasing towards those threats.

Aaron Levie, CEO of Box, operates at a frenetic pace with the mantra that “only the paranoid survive,” anxious that he could be disrupted at any time. His opts for sneakers as part of his daily uniform because they “help [him] walk faster.” He’s said, “I don’t have time for nonwork stuff,” and that seems to have worked out pretty well for him.

Travis Kalanick, CEO of Uber, is a poster child for the gladiatorial approach. He’s been quoted as saying, “You have to be a fighter, you have to be a warrior, and if not, you should go do something that is a little less disruptive. I’m bringing it, I’m not sleeping. If the other guy is sleeping, I am going to kick his ass.”

The point is not that these attitudes are bad. Quite the opposite. Aaron and Travis are impressive entrepreneurs who have managed to build incredible companies from the ground up in part because of their personalities. But glorification of the lifestyles of a handful of founders has created a culture where startups are often equated to war and founder bravado can air on the absurd. Francisco Dao commented on this trend in his post, “Hustle and Flow,” ridiculing founders who say things like, “you can sleep when you’re dead.”

When I hear founders make comments like that, it reminds me of a Michael Scott quote in “The Office.” When asked, “What do you think are your greatest strengths as a manager?” he replies, “Why don’t I tell you what my greatest weaknesses are? I work too hard. I care too much. And sometimes I can be too invested in my job.”

Generally accepted abuses of personal health, like lack of sleep, a poor diet and no exercise, are proudly worn on the sleeves of many entrepreneurs as accomplishments. I’m interested in accounts of entrepreneurs who go about it differently, being intensely focused on building an amazing product and business while also maintaining a balanced life.

I aspire to be an exemplar of the laid back entrepreneur. I want to be known for my obsession with Treatings but also able to admit to not losing sleep (because I do sleep!) over inevitable speed bumps without losing credibility. The only problem is that this doesn’t make for a gripping story… and I’m not successful.

Oh ya, and when I told Paul that the inspiration for this post was feeling defensive for being categorized as easy-going, his response was, “I mean… I don’t think you’re that easy-going.”

This post was originally published on PandoDaily.

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Avoid networking events marketed like a crappy apartment on Craigslist and other pro tips

As a first-time startup founder, one fundamental question I struggle with is “How is my time best spent?” Do I focus on productuser acquisition or customer acquisition? Or maybe I should just hang out on Twitter all day and have an existential crisis every time I catch a whiff of someone else building a professional networking platform. So many options to choose from.

One unexpected beast that’s reared it’s time-eating head is the infinite loop of networking events. The longer I’m in the NYC startup community, the more invitations accumulate in my mailbox for happy hours, mixers, roundtables, pitch competitions, and conferences. Some seem benign — town halls where like-minded people gather to listen to a speaker. Others sound more intense, with nebulous descriptions like “power pitching and power networking.” I’m not sure what power networking is, but I have a hunch arm-wrestling and business card paper cuts are involved.

When I quit my finance job to start Treatings, these kinds of events were a boon. My professional and social network was fairly homogenous, which was the impetus for starting Treatings in the first place. I wanted to speak with people who had transitioned from investment banking to a startup, but found peers with relevant experience difficult to find and meet.

My co-founder Paul and I borrowed from online dating sites, creating a platform where you can propose coffee meetings with fellow members to learn about companies and skills of interest and see who’s interested in treating you to a coffee (or drink). Now that our New York City beta is live, we have a platform to reach out to strangers who have experience we’re interested in. That said, right after jettisoning our corporate jobs, networking events seemed to be our only portal into the startup community.

As a non-technical co-founder, I assumed one of my responsibilities was to go to as many events as possible. I attended countless Meetups, as well as networking events sponsored by local startups, investors and co-working spaces. These helped me get a better feeling for the startup landscape, learning about the players (prominent founders, startups, investors) and abundant resources available, such as General Assembly and Skillshare.

While initially helpful, I found these events sported diminishing marginal returns. Not all networking events are created equal, but I’ve noticed some parallels.

When you’re pinching pennies like we are, even cold pizza sounds appetizing when it’s on the house, so free food can be enough to rationalize attending any event. Sometimes you’ll find a diamond, or should I say shrimp, in the rough. When I walk into an event and see cocktail shrimp, it’s like Christmas has come early. This past week when a law firm hosting an event provided everything from sushi to berry skewers, I had to stop myself  from stuffing sashimi in my Jansport.

Moving from caloric to educational satiation, sometimes these events are centered on an inspiring guest speaker. By being a member of the New York Tech Meetup, I entered a raffle to see Ray Kurzweil speak last year. I was fortunate enough to receive tickets and two hours later I was on the roof of a SoHo office listening to the futurist say things like, “and maybe it wouldn’t be such a bad thing if animals could vote.”

I was only a few months removed from a cubicle at a bank and had never heard anyone like him speak. Something he said that particularly stuck with me (besides giving animals civil liberties) was, “You don’t build products for today, you build them for tomorrow.” Technologists and experienced product managers might find this elementary, but it had an impact on me. When we started Treatings I was focused on the existing behavior of people who wanted to meet professionals outside their network. I needed to adopt a more forward-looking perspective to anticipate paradigm shifts in technology and consumer behavior. This is a simple example of a viewpoint I might have missed if I didn’t step outside of my insular network.

I’ve attended many great panel discussions and speakers. The events I’m skeptical of are those where the major draw is networking. Or as some events are detailed in e-mail newsletters, “NETWORKING!!”

Pro-tip: Any time a networking event is marketed like a crappy apartment on Craigslist run the other way.

Even when big name speakers are present, I’ve found that much of the potential networking value centers around serendipitous connections with fellow attendees. At most events, these latent connections remain just that — undiscovered.

A prime example is at startup pitch events, where VCs are often given red name tags. This inevitably precipitates a pitching frenzy, with a sea of founders swarming the few red name tags, lining up single file while silently rehearsing their elevator pitch. I’ve been guilty of spending an entire event waiting in various lines to speak with people who don’t have the energy or time to have a meaningful conversation.

It doesn’t help that most entrepreneurs are transactional and competitive. Introduce a limited commodity (investors, prolific entrepreneur, etc.) into a room full of founders and it’s no surprise when everyone falls in line vying for face-time. By the way, this is someone who minutes earlier probably announced, “The best way to get in touch is through a warm introduction.”

The irony is that you’re often surrounded by peers with more relevant insights than the senior person in the front of the room. Whether looking for product feedback, funding advice or anything else, chances are that peers in the room have recent, pertinent experience.

One problem, besides the tendency of everyone to focus on a handful of luminaries, there is often little transparency around who is attending the event and why they’re there. You have to hope you serendipitously end up speaking to someone with whom you can have a mutually beneficial conversation, and even then you may not unearth shared interests.

In learning about task prioritization through diligent mismanagement of my own time, I’ve resolved to cut out most things that take me away from the product and our users. This hasn’t left a networking void in my life, since I can reach out to Treatings users who have experience I need in and set up one-on-one conversations over coffee.

That said, cutting out networking events has left a pigs-in-a-blanket void in my life… but that’s nothing that a few salt packets and a stick of butter can’t replicate.

This post was originally published on PandoDaily.

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A bootstrapper’s survival guide

There’s no shortage of articles and videos providing inside looks at successful entrepreneurs and their startups. You can learn about the founder’s vespa of choice, what discipline of yoga is provided to align employee’s qi, and the kind of free beer that can disrupt that qi.

This is not one of these accounts. Instead, it’s a bootstrapper’s survival guide, strategies for getting your startup off the ground on as little money as possible. In other words, these are things my co-founder Paul and I couldn’t live without as we build our startup, Treatings.

Housing

In this series I’ve exhausted the stairway to heaven, AKA the bunk bed Paul and I share. But, for anyone considering following in our cheap footsteps, I do have one housekeeping note: at Bed, Bath & Beyond they only sell Twin XL bedsheets at the beginning of college semesters. If you try to purchase them off-cycle you’re in for an embarrassing conversation. When I asked, “I didn’t see any Twin XL sheets, where do you keep those?“ the well-meaning employee replied, “No, I don’t think you’re looking for Twin XL sheets, those are only for dorm room furniture.”

Awkward…

Savings from my previous apartment: $1,100/month (admittedly, I was overspending on my last apartment), plus Paul, my cofounder/roommate’s savings: also $1,100, for a grand total of $2,200.

Transportation

The days of black cars sponsored by Wall Street clients are a distant memory. Whereas two years ago, when I worked at an investment bank, I might have been the guy shaking his head disapprovingly behind tinted windows as skittish bikers wove in and out of traffic, dodging cars, doors and pedestrians, now I’m the scared asshole on the bike. If you rely on a bike in NYC, make sure to have Yelp at the ready for when your bike is “relieved” of its front tire, so you can find the cheapest replacement within a 5-mile radius.

Savings over monthly subway pass: $1,000/year.

Office Space

With a team of two and no funding, it’s difficult to justify (afford) office space. Instead, we use a library. New York University Bobst Library to be exact. We discovered we could leverage an old apartment address to get “Friends of the Library” passes. Advantages: an annual pass costs less than one month’s rent at a standard coworking space. Disadvantages: even a whisper can often elicit passive aggressive stares from sleep-deprived students, and when exam time comes around finding vacant seats is a lost cause. In addition, we have no private space where we can invite people over for meetings.

Savings over co-working space: $5,000/year.

Meeting Space

So, where do we receive in-person feedback? The nice thing about creating a professional networking platform to connect peers over coffee is that we have an excuse to schedule our own meetings in coffee shops. If you’ve received an “In the spirit of Treatings, let’s meet at [coffee shop x],” it’s because the NYU Library doesn’t take kindly to those who aren’t students, financial donors or Paul and me. We’ve mapped out an Oregon Trail of coffee shops to frequent, with the requirements being reliable Wi-Fi, cheap refills and a lax policy on camping out.

Savings: -$750/year (we’ll chalk this one up as a loss, given the exorbitant amount of money we spend on coffee.)

“Thank You For Your Criticism. I Appreciate It and Am Not At All Defensive” Smile

When soliciting feedback on Treatings, we always need this smile in our back pockets. Naysayers and criticism are in no short supply. I’ve realized that you can never appeal to everyone, and if you do that can even be a negative signal. As others have said, if you’re building a product for everyone, you’re building it for no one. I’ve experimented with the “interrupt and defend” approach, with no success, so my new resolution is to slap a smile on my face and just listen.

Savings: Face (Don’t look like a defensive prick)

Food

We’ve conducted due diligence on establishments near our apartment and the library, crunching the numbers on the protein-to-dollar math. On more than one occasion, Paul has sheepishly asked an employee of a restaurant, “How many shrimp, if you were to guess, come in this dish?” Lunch is often at a takeout spot that offers a discount for those who arrive on bike. We’ve even pinpointed the server who is most generous with portions, forgoing the store altogether if he isn’t around. Dinner is a toss-up, as it often depends on the 20 percent off Seamless rotation. If we’re desperate to get out of the library, there’s a nearby bar that has an extended happy hour and lets us order delivery food.

Savings: I’m netting even on this one, since dinner and weekend work meals were paid for in my previous job but I was eating out more often.

Lawyers

When we were looking to incorporate, founders warned us that the one area where we shouldn’t cut corners is legal help. We were fortunate to find capable lawyers who don’t care about that whole payment thing, or at least collecting on the billable hours we’ve been accruing. There are numerous startup-friendly law firms that will defer payment until after the startup raises funding.

Savings: Your company. One of many things we were alerted to by our lawyers was 83(b) elections. Failure to file proper paperwork at the outset can result in company-jeopardizing tax and legal consequences.

Explicable Domain Name

We failed the “explicable” test. When meeting people, whether at pre-arranged meetings or accosting them in Washington Square Park, an elementary question we’ll receive is “So, where do I find you, is it just treatings dot com?” The .com domain was taken by someone ringfencing a similar-sounding site name, so we settled on treatin.gs. God, this was a bad decision. We’ve burned an embarrassing amount of time trying to communicate this domain. Most people have never visited a site with a .gs domain, so our poor choice has wasted us time (a lot of arm-moving and gesturing to paint in the air where the dot is in the name) and cost our visitors. Last week we switched the domain to treatings.co. This still isn’t ideal, but at least we won’t receive any more e-mails ending with, “I’ll be sure to check out treatings.gs.”

Savings: Time and legitimacy

Maybe one day we’ll be featured in one of those office video tours, with Paul and I pontificating on our culture while in the background the Customer Experience Ninja can be seen pulling the trigger of her quadruple barrel NERF gun aimed at the barrel-rolling Chief Happiness Officer.

Until then, we’ll make do with the bare necessities.

This post was originally published on PandoDaily.

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In lieu of investors, how we breathe down our own necks

Bootstrapping our company has extended our runway.

I realize that might sound counterintuitive, but it has given us more time (albeit with fewer resources) to find product/market fit. If we had raised money last year, when all we had were wireframes and aspirations, it would have likely ended poorly.

It’s important for us to remember that a runway is simply a means to an end. The objective isn’t to focus on extending it. Rather it’s to get off the ground and be self-sustaining so that we don’t need to worry about it. Neither of us want our personal savings to fund a bridge to nowhere.

As we’ve spent the past year searching for product/market fit we have stayed true to our goal: to build a networking platform that makes it easy for professionals to meet new people. Treatings is a community of people open to sharing their work over a coffee/drink, so there are a lot of nuances of social dynamics we need to understand.

If we were to compare the process of building a company with constructing a house, we’ve been digging down, instead of building up, to create a solid foundation. Although this period of learning has been crucial, it’s anything but comfortable. Since my co-founder Paul and I try to test before we build, a lot of our progress is not outward-facing, or readily apparent. This, of course, promptsquestions from friends and family who are tracking our progress by monitoring the site, wondering how everything is going when they don’t see new features being built.

While it can be unpleasant to defend perceived inactivity, I’d prefer that to feeling pressured to build flashy features, fueled by funding and a ticking clock to spend that capital. While this would have satiated passive observers, I know that when Paul and I left our jobs to start Treatings we were not equipped to handle outside capital.

Founders who have raised money have warned us that as soon as you raise venture funding the house is expected to be rapidly built up, at a pace dictated more by predetermined milestones than considerations about structural integrity. If driven by cash and expectations, we likely would have started loading bells and whistles onto Treatings before establishing a solid understanding of the problem our users have and the repeatable process we are implementing to solve that problem. This would have resulted in an unsound framework.

It’s not the manufactured deadlines that I fear, just the intervention to make bold bets before we’ve established our footing. Thinking back to school, even the most diligent students benefitted from imposed deadlines. In an experiment Dan Ariely chronicles in “Predictably Irrational,” MIT students were broken into three groups. All groups had to write three main papers over the course of the semester. In Group 1 the students were allowed to set their own deadlines, in Group 2 there were no deadlines at all and in Group 3 the teacher dictated three firm deadlines. At the end of the semester, grades across the three groups were compared. Ariely found that students with the firm deadlines got the best grades and students where no deadlines were set did the worst. The surprising revelation isn’t that students procrastinate, but that “simply offering the students a tool by which they could pre-commit to deadlines helped them achieve better grades.”

So how do we apply Ariely’s findings to Treatings? We aren’t spending anyone else’s money, so we don’t have a third party dictating deadlines. That’s unfortunate. Although I’m wary of what the stipulations might be, I’m sure we’d move faster if we had VCs breathing down our necks. But, that doesn’t mean we need to resign ourselves to operating unencumbered by goals or deadlines. We should be more disciplined about setting deadlines and holding ourselves accountable.

It’s too easy to set a deadline and rationalize between the two of us why it’s okay if we miss it. People often ask, “How long could you continue bootstrapping Treatings?” The answer is that if we were to continue spending at the low rate that we’ve been (namely supporting our bunk beds and coffee habit), we could go on for another year or two. But running out of money should not be the demise of Treatings. We must force ourselves to race towards the inflection point of testing our business model, seeing if companies are willing to open their checkbooks to leverage our platform for recruiting and employer branding. If they say yes, we will be off to the races, either building out the product and team through revenue or raising venture funding. If companies say no, we should pivot or shut down Treatings altogether.

Two weeks ago we set an artificial deadline of this past Wednesday to push up changes to our site that we’ve been working on for months. We finally optimized the site for a mobile browser, added an activity feed, bolstered user profiles and provided the option for a one-click indication of interest in meeting fellow members. The deadline was “artificial” because there wasn’t a critical event that demanded that we push up these changes. At our nascent bootstrapped stage, there are rarely times when others will hold us accountable.

Unless you count my girlfriend asking when I think I’ll have my own bedroom. Then there are many times.

This post was originally published on PandoDaily.

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A bootstrapped startup’s freelancer dilemma

One of the first decisions my co-founder Paul and I had to make when starting our company, after the all-important matte vs. glossy finish business card debate, was whether to build the site ourselves.

This wasn’t a trivial question. When we left our corporate jobs neither of us had built a Web application before. We had saved money to pay someone to build a site for us, which would have saved us time and resulted in a more polished product. Alternatively, we could have learned the skills necessary to build it ourselves, an approach that takes more time but saves money and ultimately allows a team to be self-sufficient.

At first we didn’t give too much consideration to the notion that we could build Treatings without outside help. But, after being warned repeatedly by founders who’d wasted precious time and money outsourcing early prototypes, we decided to build the site ourselves. In hindsight, this was the right decision.

Although he had never developed a Web application, Paul had an academic and professional background in computer science, so he jumped into the role of CTO. The first challenge for us was to settle on what to build, which involved defining our objectives, prioritizing features accordingly and mapping out the overall user experience. Once we’d established what to build, Paul began the process of figuring out how to build it. We anticipated that our biggest challenges would be technological, butthey’ve turned out to be social.

As we’ve iterated on our professional networking platform, determining the best framework to help professionals propose coffee meetings with individuals to learn about companies/skills of interest, we’ve made a lot of mistakes. A lot of our gaffes and incorrect assumptions were only realized after releasing a series of prototypes that people could interact with. It didn’t matter that the products were unpolished. They were instrumental in shaping the framework as it stands today. We realized that the search for product/market fit takes time and lots of conversations with users. Paying someone else to build our early prototypes would have been an efficient way to waste money because many of our initial hypotheses were proved incorrect, rendering our makeshift code useless.

This summer, in preparation for onboarding our first paying customers, we decided to work with an outside developer on a freelance basis. We figured that we needed an expert to review our codebase, implement some testing to better identify bugs and optimize our site for a mobile browser before asking companies to open their checkbooks. Unfortunately, what was supposed to be a three week project is closing in on a three month project.

Prior to Treatings, I’d never hired or managed anyone before. In determining the best way to work with a freelancer, I could only reflect on management styles that I work well under. In my prior job as a junior investment banker, I did my best work when parameters for success were clearly defined but I was given the freedom to find the best way to achieve the agreed-upon goals. I brought that same mindset to working with the freelancer — we defined the scope of the project, he laid out a timeline and we gave him complete autonomy to work within the expected three week time period.

Working with the freelancer has cost us a lot of time, but we have no one to blame but ourselves. After months of building our own prototypes, we finally had someone helping us who had over a decade of experience building web applications. While we should have viewed him as a crutch, leaning on him to help us with issues like scalability that we had never dealt with, he effectively turned into a wheelchair. We were wary of getting in his way as he made changes in the codebase, and the longer the project went on the more paralyzed we became. It was as if our technical muscles had atrophied. When users would relay feedback or potential customers asked when they could test the platform, we would reply that we were held up on this project and our hands were effectively tied until it was over.

Relying wholly on a third party isn’t ideal in any situation, but it’s especially damaging when it is someone who is juggling multiple projects. Even if we were the only project the freelancer was working on, there’s an inevitable chasm between our obsession with Treatings and his. At week three of the project, when it was supposed to be completed, it was apparent that the timeline was stretched indefinitely. We did little about it. I felt privileged to have an expert working with us and didn’t want to micromanage him.

Although we offered to meet in-person and be helpful where we could to accelerate the project, overall we were too hands-off. We should have politely cut short the project when the first deadline was passed, but at that point we were incapacitated. While there are multiple other ways we should’ve handled the project differently, it’s likely the whole thing was premature.

In Geoffrey Moore’s book, “Crossing the Chasm,” he explains that “the point of greatest peril in the development of a high-tech market lies in making the transition from an early market dominated by a few visionary customers to a mainstream market dominated by a large block of customers who are predominantly pragmatists in orientation.” We may have put the cart before the horse, working with a freelancer in order to bolster technology that the mainstream market will care a lot more about than the early adopters we need to be focused on now. In reality, we don’t have so much traffic to make scalability a pressing concern.

We have to get those first few customers who are willing to pay for Treatings in spite of bugs. We were too quick to bring on an expert, subconsciously trying to put time and technology in-between us and our come-to-jesus moment of asking companies to open their checkbooks. We should have delayed this project until after we had revenue coming in the door, even if just a little. Being self-reliant leaves all accountability with the founding team, because it’s too easy to blame someone else for missed deadlines or product failings. If potential customers are resistant to fork over money because of minor technical bugs, it could be a red flag that we aren’t solving a dire enough problem.

This past week we decided that now was an appropriate time to end the project. Paul is tying together loose ends and we plan to push the site changes live next week. Then, we’ll work to get back into a process of continuous and incremental development and deployment. We’ve had good experiences working with freelancers on other aspects of the site, I just think it was jumping the gun to work with an expert developer at this stage.

For anyone still reading this post: Please hold us accountable for returning to self-sufficiency by giving us grief if the site is still not optimized for mobile by next Sunday.

By “grief,” I mean “the names of three freelance Ruby on Rails developers.”

This post was originally published on PandoDaily.

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