Stealth Mode

As I’m sure it’s been for everyone, 2016 has been a helluva year. I’ve learned a lot working on my startup, Handstand, and thought I’d highlight three learnings that might be helpful for others building companies of their own.

In 2016 I took a leap. After the very first week of the year, one in which I learned I was being laid off along with the rest of my company, I have spent the majority of the year working on my own bootstrapped startup. 

I’ve learned a lot, failed many times, and realized how much I love the craziness of building a business. 

What started as a fun side project has turned into my career (for better or worse!) but this year set the foundation for a big 2017 with successful events in San Francisco, Seattle, DC, and Boston. 

I wanted to share three specific learnings from this first full “all-in” year in case others are starting or thinking of starting something.

1. This Shit Is Hard

There’s just no way around it. This was both the most rewarding and most frustrating year of my professional life.

I’ve had days this year where it felt like I couldn’t do anything right. Sponsors rejecting me, people not being flexible with gameday venues, zero signups. Days with that trifecta and more 100% happened this year.

But the most important thing is to just keep going. Pick back up, keep pounding, and give it another shot. 

No one has the answers. It’s up to us to solve these problems. How do we get the right sponsors excited, involved, and paying us for that value? How do we find the absolute best places to start and end the day to delight our players? And how in the world do we get players in the first place? Woof. Breathe. Try not to freak out, but these three questions basically incapsulate the larger question of “How do we build a successful event?”

We ended up finding sponsors, getting venues to host us, and attracting an amazing community of people to play. The difficulty makes solving these problems (and like a million others) taste so sweet. And it’s why when they get solved, I believe in the answer with a degree of certainty that can’t be matched when someone else tells me how to do things (and gives me the answer).

But the persistence of things being hard is something that I’ve come to realize is inevitable and omnipresent. There will never be a time where I’ll think this is easy. And that’s okay. I don’t think I’d enjoy it any other way.

2. Always Be A Beginner

One of the things I’ve realized I like the most in my work is finding things I either a) have never tried or b) am knowingly not good at and trying them. 

Growing up, I feel like I was always encouraged to try things. Music, sports, acting. Every kid gets involved in things and then figures out what they enjoy and what they’re good at and gets naturally pushed or pulled into those activities.

Doing that with new software programs, marketing strategies, and sales techniques feels very similar. Except this time, I’m embracing the experience of being a newbie (didn’t enjoy being bad at art class nearly as much).

Part of this has been a mindset of mine. In the last few months, we’ve turned a good amount of our focus to working with companies to do custom scavenger hunts for them for team building and as a part of their onboarding of new hires (speaking of, reach out if you want to chat about this for your company :).

At this point, my role is sales. Find opportunities for us and close the ones where there is a good fit. I’ve always had sales be a part of my job at Davidson, Curious, and Lovely, but this is the first time I’ve explicitly been responsible for sales. 

Of course when I started out I thought I’d just crush it no problem and everyone would want what we have to offer. Not so much. After a few attempts, I realized I could just humble myself and help myself a lot. I’ve read Traction, Predictable Revenue, Getting to Yes, and started having meetings with friends who are fully in sales to understand best practices better. Not only is choosing to be a beginner at sales intellectually stimulating, I’m actually getting better at it. 

Part of this initial uptick in learning and success has just been embracing failures as learnings and iterating, building, and trying new things. I think this is an attribute I want to keep with me throughout the entirety of my professional career and even in my personal life: never be comfortable with what I know. There’s always more to learn and new levels to get to. Being bad at something or being a beginner is just the start to what could be a long journey to being an expert.

3. Nothing Replaces Sweat / No Days Off

There are no shortcuts in this. One of the quotes I really like that has stuck with me is “If you work hard for long enough, you might be lucky enough for someone to call you an overnight success.”

Just putting in hustle and effort every day keeps us on a path to do better tomorrow than we did today. There is simply no technique, hack, or easy way to replicate what comes with just purely consistent application. It’s nice when there’s clear examples of hard work paying off, but I’ve realized that working on Handstand is similar to the mindset of the training I used to do for soccer. There’s so much time put in, that you have to enjoy the hard work and the process. 

This learning does not mean that I don’t take any days off. What I mean by No Days Off is it feels like I can’t have an “off” work day. Maybe it should be No Off Days instead. If I’m not sharp, I’m actively holding the company as a whole back. Those days that used to happen where you hang a little longer at the water cooler (or whatever most startups have now—pool table?) just can’t happen anymore. I literally installed an app on my desktop called Self Control that lets me block certain websites from my own browser for a period of time I choose. Gotta shut Facebook out sometimes. 

Sustained pure and constant hustle and incessant focus every day are impossible. But holding them as the standard and striving for that perfection is what gets me as close as I can to achieving my potential.

Finding my way to the startup big leagues of San Francisco was no easy task. I probably talked to 150+ people along the way spanning consulting, venture capital, and startup companies. Many were Davidson College alumni who went above and beyond to introduce me to people in their networks and point me in the right direction.

Intent on paying it forward (I still am), I was pleased to hear from a graduating Davidson senior last year. We’ll call him Richard. Richard was in the throws of a difficult time for any college senior, especially at Davidson. He was trying to figure out what he wanted to do with his life amidst an environment of unspoken but very real pressure applied by parents (“any job leads Josh?”), classmates (“I know exactly what I’m doing next year — lets party!”), and the real world (“Earth to Josh. It’s your bank account. Feed me.”).

I treated Richard as I’d been treated by startup friendlies before me — I asked him lots of questions to better understand his interests and introduced him to anyone I thought could be useful for him to talk to.

I saw in Richard a lot of what I had been when I first ventured to San Francisco: a smart, hungry kid who just wanted to make an impact, contribute, and learn as much as possible. In my pseudo-mentorship role, I continued to stoke his confidence that he would be a huge asset to many different companies based on his passion, his ability to synthesize information into actionable insights, and his humble willingness to dig in and contribute. (I wrote a longer post about why Liberal Arts students make great startup hires here.)

I was already pumped for him and proud that he’d ignored the pressures seniors (again, especially at Davidson) face to follow a traditional law/banking/consulting/medical path. A couple months later, after another visit to the Bay for a final round interview, Richard updated me that he was forgoing working for any Bay Area startups and starting his own company in Atlanta. I was shocked but incredibly excited for him. Richard had already learned what has becoming increasingly obvious to me:

There is no such thing as risk.

Okay, fine, there is such a thing, but it’s not nearly as scary as you think. Especially if you’re a twenty-something. I didn’t get to this realization or clarity all at once. Indeed, I’d subjected myself and in some ways succumbed to the very societal expectations Richard bucked.

When I joined Lovely, I was looking for a much bigger opportunity to learn. I’d come from a good foundation at Curious.com and just wanted to make sure I’d grow professionally in whatever came next. Role and opportunity were what I optimized for and under those conditions I did very well. I was given the reins immediately to run with Lovely Direct and over the course of a year, I learned a ton and made an impact in the San Francisco rental market helping hundreds of people find a place to live.

The one complaint in the back of my mind when I signed my offer letter and that grew larger in my mind over time came in the form of a question: Am I risking enough here? Lovely had been acquired by Rentpath when I joined and much of the macro opportunity was a long way off. It was a question I grappled with often and but always pushed past given how much I was learning.

Fast forward a year later and (quite ironically) I’m laid off from my Lovely job. I’m taking a step back to determine what’s important to me and how the larger arc of my career should bend now. Big company vs. small. Early vs. growth stage. These are things on my mind. But it is clear to me that whatever my next step is (and I’m planning on making a final decision soon) I will make it with the realization that there is no such thing as risk.

When I do the math it’s really quite simple. No mortgage, no kids, no loans. Relatively low expenses (by SF standards) and a good amount of savings. I’ve played through the worst case scenarios in my head already. If I work on my company, Handstand, full-time and it fails, someone will view me as more hirable and capable than I am today. I’ll learn so much and be better for the experience. If I burn through my money I’ll be able to earn it back.

Ultimately, if I ignore the societal pressure that exists, even in San Francisco, to find the nominal stability of working for someone else, the only actual risk is “can I cover my expenses and continue to live?” to which I feel confident the answer is yes.

Even if I join another company, I’ll do it with this concrete knowledge and belief. I’ve built a network and skill set that the market views as desirable and hirable. If the next company I join fails, I’ll be where I am now, which really isn’t so bad at all.

I recently stumbled across an Andy Dunn (Bonobos CEO) blog post I’d read before called “The Risk Not Taken.” I especially like this passage:

“The risk is not in doing something that feels risky. The risk is in not doing something that feels risky.”

This resonates. Is there a worse feeling than the feeling of regret? Than feeling so close to something and not taking a chance? I’ve always found that doing something that scares me is often when I learn the most about myself. Moving to San Francisco, far away from family and friends, being a good example. For me to live with a clear and honest conscience, I have to know I’m giving all that I have. And that means to reject regrets, take positive steps forward, and at this time in my life, block out risk.

As I continued with Dunn’s post, he really could have been talking directly to me:

“The risk you are thinking of is scary, but here’s the good news: You’ll figure it out. If you have something you want to do, it might later feel — with some luck — that the universe conspired to enable you to do it. That’s certainly how I feel. So what are you waiting for? Your eighty-year old self asks nothing of you but this.”

Even in everyday life I see signs that support ignoring risk. I used to pass a big piece of artwork on my way to Lovely that said “It is a good idea.” A few weekends ago I passed a building in LA that proclaimed in a loud voice (to me at least) “Live a good story.” That’s exactly what I want to do.

I am fortunate for so many reasons that I’m able to exempt myself from risk. I’m forever grateful for my Davidson education because without it, I would be far less confident in my worst case scenario. I’m thankful to live in a place that encourages trying new things. Experimenting. Viewing the world not for what it is but what it could be. I have an absurdly supportive family, girlfriend, and friends who believe in me sometimes more than I believe in myself.

People say “don’t look down” when you do something that is supposed to be scary. But sometimes looking down gives you the jolt of adrenalin to move forward. Forward it is.

Over the past year I’ve worked at Lovely on an innovative new product calledLovely Direct. At a high level it was a technology product for leasing rental properties for property owners and managers. We took care of the legwork (photos, marketing, showing, screening, etc.) and let our customers make the important decisions on price and tenants. Despite impressive growth andcustomers loving us the Lovely SF office was all laid off January 7th and Lovely Direct is shutting down. Despite the sadness I feel for leaving such a great team, I learned a ton in this past year and I’ve tried to distill some of those learnings below in the hopes that others might benefit.

The first week of 2016 was one of the most eventful of my whole life. After a great two weeks in Maine with Kate and her family, I was ready to hit the ground running and make shit happen in 2016. But as the commercials say, life comes at you fast. Monday I got a car window smashed (nothing taken), Tuesday was my 27th birthday (an awesome day), and Thursday I found out I was out of a job. It was an amazing run in just under a year and despite having no control over the loss of our product and team, I know these learnings will leave me in a much better place — whatever I end up doing next. Among other learnings like, don’t forget to label your almond butter (shoutout Affan!) and never miss an opportunity for karaoke, here’s what I’ll take with me most from building Lovely Direct:

Finding Product Market Fit can really be painful.

Failure is essential. To everything.

A great culture with great people yields results. Period.

A good boss can set the stage for success.

Capitalism can be cruel.

The pains of finding product-market fit

Our product was a new idea. Taking a traditionally entirely manual process and making it smoother with technology is exactly the type of challenge I like. I was brought on specifically to work on Lovely Direct and at first we talked about it as “the leasing project” before it had a name. We started with one operations person, Leah (hire her!), and no full-time engineers. People joked it was JLAAS, Josh and Leah as a service.

The first challenge we had was determining if this was a viable product in the first place and if the market would support us. I hit the streets and crashed open houses for two weeks straight, pitching landlords and property managers on our automated leasing solution. And…people hated it. I heard things like “this will never work” and “the leasing process will always need a human touch.” Some of this feedback hurt but mostly it was extremely useful.

We changed our rhetoric and messaging around the product and started to see people respond positively. Our first customers gave us units to work on.

These first few units were exploratory for us. What did we need to do to meet expectations and lease a unit? We had no real tech built into the product at this point. We sent emails with updates and everything was bare bones. Ultimately we found that people were pumped to have us do the work for them, even if there were bumps along the way.

One of the best things we did as we continued to build out our team was to interview everyone we worked with at the conclusion of their process with us. We learned where the real pain-points were in the process and were able to tweak our offering. Some people would rant at us about how terribly we screwed up this or that and then at the end of the interview when we asked if they would use us again they’d say “absolutely, of course.”

By the end of Lovely Direct we didn’t yet have a full-featured product but were were close. And it was all driven by this at times harsh feedback loop. When we were able to get feedback from the market, funnel those learnings internally to develop the product and inform the messaging, and then repeat the process, we scratched the surface of product-market fit.

Failure is everything

Related to the first point. Lovely Direct was the first time in my career where I realized how crucial failure is to success. It sounds backwards, but without our failures, there’s no way we could have scaled to nearly 100 units in the course of 9 months.

Risking only personal pride and ego talking to landlords at their open houses was the best way to get rejected and learn about our assumptions at a high level. Whenever someone said no to our product, assuming it wasn’t a loud and offended “NO!” (which I got a few times), I’d ask what specifically turned them off about the product and why it didn’t work for them. Lots of those “not for me” responses led to our “sure, I’ll give this a try” answers.

As we started to nail the product and sold it more successfully, we brought on so many units that we broke our own internal operations practices. We were able to grind through those tough units and re-engineer our process for success. Breaking things and failing forced us to be more efficient.

It may not be comfortable, but pushing to the point of failure made us more efficient and helped us sell better.

Culture yields results

The Lovely office is the best place I’ve ever worked. People here were smart, driven, and really freaking fun. I talked with Doug Wormhoudt, our co-founder, at our holiday party about what he hires for and it stuck with me. He looked for people who were passionate, intelligent, curious, and humble. Everyone here embodied those traits and then some.

The work we did was sometimes a grind but doing it with people here was always a joy. I never dreaded going into work and I don’t think anyone did. When you hire good people, foster a culture where people are pumped to show up, and let them loose, great things can happen. That’s something I’ll always remember and look for in any place I work. Without a great culture, products and businesses will always stutter.

Specifically for Lovely Direct, people would raise their hands to contribute outside of their core functions at work because they knew there was an opportunity to help the team. From taking on showings to lending a hand on operations, people cared about the team and end result more than themselves. I’ll always value and look for that in any place I work.

Bosses are important

At Lovely, I had a friend as my boss, Erik Preston (hire him too!). Erik was someone I got to know when I first looked to move out to SF. We kept in touch and he eventually convinced me to work on Lovely Direct. He told me in the hiring process that his style was to bring on smart people and get out of their way. I knew I could learn from him and thought of him as someone I could model my career after in some ways.

True to his word, he let me run free at Lovely. He removed obstacles, proactively put me in positions to grow and learn, and genuinely found me a role I could succeed in.

Up until I worked on Lovely Direct, I always thought good people can shine no matter their situation. I still believe that but I also firmly believe that a good boss can accelerate growth personally and professionally where an individual can be limited on their own.

Harsh capitalism

The toughest lesson learned. Lovely Direct was an absolute success no matter how you measure it. We had a Net Promoter Score of +20, worked with some of the biggest property owners and managers in San Francisco, and successfully leased almost 100 units in a very short time frame.

In the end, none of this mattered. The Rentpath board is controlled by a private equity firm and they made a cost-cutting move to take the functions of our office to Atlanta. This just opened my eyes in a new way. My biggest complaint about Lovely was that it wasn’t a big enough risk (larger post on that later) and that seems a little silly now.

Final Thoughts

I grew a lot in my one year at Lovely. These are great people and this experience will serve me well in my life going forward personally and professionally. Can’t wait to apply these learnings to what’s next. Long Live Lovely.

My friends are crazy. This group thrives on ludicrous adventures like running rim to rim through the Grand Canyon, hiking in Zion National Park’s slot canyons, running the Lost Coast, and summiting peaks in Glacier National Park. 

These exhausting, “Type 2” fun adventures helped us coin the term “co-discovery.” Co-discovery means stretching limits and learning more about yourself while doing something new, sharing in that experience with close friends to make it more meaningful.

Our goal was to deliver co-discovery to as many people as we could. What we created was The SF Hunt — an epic 12-hour, tech-enabled, 100-riddle-filled, 450 plus-person, physically and mentally demanding, team scavenger hunt adventure through San Francisco.

Here's how it worked:

We didn’t know what the day would hold but the finished product turned out to be even better than we could have hoped for. Being a part of this micro startup for an intense few months was an adventure all on its own with some healthy co-discovery to boot. Here are a few things I learned.

1. Dream big (and crazy) but obsess over the details Start outlandishly big! Stretch your imagination and think about what the absolute home-run scenario would be. Then go a little grander. In our design process we made decisions with the goal of growing beyond San Francisco. Things like the name, “The SF Hunt”, were conceived with the question of “if we did this again, here or elsewhere, how could it be scaled?”

With previous organized shenanigans we planned, typically the number of participants became unwieldy for either financial or safety reasons. The collective decision was made (from the start) to open The Hunt up to the general public, charge for it, and blow the doors off everything we’d done before.

In any startup, knowing your customer is key, but that problem was solved easily — we were our own target customers! With a grand vision in mind of 400+ people running and biking around San Francisco (did I mention The Hunt did not allow driving/riding in cars?!), we honed in and built backwards from a user experience we would have wanted for ourselves.

We obsessed over the seemingly small details. Everything from the official hashtag (#TheHuntIsOnSF), geographic radius around each riddle location, day-of operations, logo design, communication timelines, lists of potential sponsors, and more were combed over again and again. There were probably more than 10 drafts of the 100 riddles, but the obsession paid off in the final product.

Starting from our grand vision, knowing our customer, and then building a detailed experience from that user perspective ultimately translated into the final product.

2. Fill as many seats as you can with varied skill sets Not only did we have a passionate team of organizers, we had varied skillsets. Within our group of 8, we covered design, strategy, web development, marketing, business development, finance, operations, and video production (check out our hype and wrap-up videos!). 

The tech was amazing, beautifully designed and functional. But without marketing we don’t have 450-plus participants. The design was clean and beautiful. But without the backend functionality, we get no value from it. Sponsors are fun to have but they mean nothing without customers. 

Each Huntmaster stepped up and contributed in his or her area of expertise and far beyond (seriously, who is an expert in writing riddles?!), but without these varied skillsets to start with, the end user experience would have been drastically different—and probably not as good.

The Huntmasters aka the Dream Team

3. Divide ownership and communicate clearly We learned this the hard way. The biggest advantage of a small company is its ability to be nimble and move quickly. We took too long to delineate clear roles and deliverables and we could have gone faster with our decision-making.

Consensus shouldn’t be the goal of every decision. If an organization is structured correctly, the person in the right position has the information to make the best call for the group. Collective buy-in is easier when ownership is clear and decision makers are known. We found this to be a huge opportunity for us to grow.

4. Think on your feet To counter my last point, our team was amazing at working through problems on game day. Registration proved to be a madhouse with over 450 people arriving nearly all at once. Our initial system for checking people in optimized for signed waivers (whatup legal team) and was going far too slow. On the fly we made the call to announce instructions intermittently over our microphone and get Hunters as prepared as possible by the time they made it to the front of the line. 

The scene at registration. #Mayhem

The learning here—and this was reiterated a few times throughout the day—is that, although it’s important to have a blueprint for how everything will unfold, the blueprint is just a draft. Solve the situation at hand.

5. Energy and passion are contagious People were shocked when we told them we put this together during our nights and weekends. All of us had experienced co-discovery and our collective desire to deliver a memorable experience drove us more than signups or dollars or anything else.

On game day, people saw how amped we were and it set the tone from the very start. Teams that weren’t even planning on competing to win suddenly snapped into gear. Hunters fed off of our excitement and we fed off of how much fun they were having. A virtuous cycle made possible because we poured ourselves so wholly into something we believed in.

6. (BONUS!) People love competition, prizes, community Probably not a surprise here, but Hunters latched onto all of these things to have a great day. We built in some bonus riddles (essentially experiences) under the pretense that a 12-hour day might yield some weary Hunters. Most people were so wrapped up in the game and solving riddles, they didn’t want to do the experiences!

That said, all of this came together when we had a treasure hunt in the middle of the day. With 100 flags covering Ocean Beach and treasure chests (with prizes) underneath 16 of them, teams raced to dig up buried treasure. I led our partnership effort in securing 16 sponsorships and over $10,000 in donated prizes — many of which were uncovered in this mayhem.

Buried treasure!

Throughout the day, teams had to wear SF Hunt buffs to denote they were in the game. The treasure hunt (and a few other bonus riddles) along with spontaneous run-ins between teams fostered a micro-community where people felt apart of something bigger than themselves. The co-discovery magic between Hunters was incredible. Sprawled across the city, people were united by competition—the feeling of being on the inside of a crazy adventure.

At the end of the day, people told us things like “I couldn’t be more exhausted, but that was the most fun thing I’ve ever done in San Francisco.” We’ll take it. And I can’t wait to do this all again.

Honorable mention lessons learned:  · Design simple (it always gets complex) · Focus on the user experience · Tell everyone you know · There comes a time when all you need to do is execute · Laugh along the way · Reflect on how far you’ve come once it’s over

If you missed out on this year’s SF Hunt and want to make sure you catch it next year, head to our website and drop us your email address. We’ll keep you informed.

Dear Average Startup Employee,

You look the same today as you did yesterday. Awkward jeans, floppy hair, and a hoodie. Don’t worry, I say that with love. You’re killing the look.

Let me talk to you for a minute. It’s not news that startups are chaotic, fast-moving, and generally less structured than larger companies. You’ve already experienced that roles within your company are symptomatic of this environment with malleable priorities and core competencies. 

In a funding environment that rewards continually getting ahead and making outsized gains, your contributions could disproportionately influence the trajectory of the business—good or bad. With that in mind here’s three things that can help you contribute to that nice up-and-to-the-right graph.

Think like your manager and/or CEO

No matter what level of the organization you’re in, elevate your thinking to a management level. Ask yourself how your team or your individual contribution could make the CEO’s job easier. Anticipate the company’s biggest risks and opportunities and develop a perspective outside your individual competency. This way when you have an opportunity to speak with your manager or CEO, you’re offering another look at the whole business, not just your role.

The more practiced you get at thinking like a higher-up, you’ll realize how much more work there is to be done, which leads me to my next point…

Give yourself work

"What? I already have work. I worked hard to get this opportunity in the first place." I hear you Joey Average, I hear you. But this is the most clear way to stand out and make a real difference. Imagine you’re the CEO (you just did remember) and one of your employees drops by your office to drop off a report on the exact research or information you’ve been needing. From a management standpoint, what could be more pleasing than knowing that your employees are aware of the issues the company faces and are proactively contributing to solving them?

The work you give yourself should be some combination of the following:

An opportunity for professional development

Outside your core responsibilities

A problem you’re curious about

A project that will add value to someone else in your company

Don’t just complete these additional projects for your CEO or manager. The extra project should be something you enjoy and look forward to doing. If it’s really outside your job, there’s a good chance you’ll be spending non-work hours on it and you want to make sure you’re invested in not only finishing but producing something valuable. (For a more in depth look at side projects in general, check out Andrew Dumont's blog post.)

Worst case scenario you add a little more work and/or stress to your plate. Get over it—there’s more where that came from no matter what. But if all goes right, you’ll add value to your company, endear yourself to your boss and/or management, and hopefully learn something along the way (that you may not have otherwise).

Execute

Okay so this isn’t necessarily directly related to being proactive, but it is certainly the most important point here. Lots of people can think (even act) like the CEO and give themselves projects to work on. The difference between these people and those who move the needle is the drive to actually push through and finish projects. It’s entirely possible that you will be the person most invested in the project’s completion so don’t wait for an outside due date to motivate yourself. 

Managers lose patience with big talkers. People who are big on hype and low on results don’t last long. Conversely, if you surprise your manager with a project you think is worthy and then deliver results on it, be around for a while. Ultimately, much of your success will come down to your own ability to prioritize and manage your time. With tasks that you’ve added to your own plate—albeit high value ones—you’ll need to know how to continue to accomplish what’s expected of you in your main role.

Beyond the face value of the project, you’ll demonstrate that you’re capable of handling more projects and/or responsibility, and maybe even discover a new skillset in the process.

Last week I had the good fortune to be invited to the 9th Annual DukeGen Startup Showcase event. This event is put on by a Duke alumni organization called DukeGen which was formed by a couple of Duke alumni volunteers who wanted to make it easier for Dukies to help other Dukies launch startups, build startups, or find startups to work for.

This was my first time going to a pitch event (kind of surprised it took me this long) and it was pretty eye-opening. Duke alumni (undergrad and graduate) presented their companies for seven minutes each and each presentation was followed by three minutes of questions from the panel of investors/judges.

Here is a list of the companies that presented:

Crowdtunes – Digital cloud-based jukebox

Rocketbolt – Customer conversion tool for SMB websites

EasyNDA – Enterprise NDA management

Coheezion – Automated data analytics for clinical trials

All9s – Vendor-agnostic replication and recovery solution for cloud-based data

Fawn – Live photo broadcasting

Final Card – Secure digital credit cards

 Here are five major takeaways from checking out this event.

 1.    Pitching is super hard

The quality of pitches was all over the map with some people far more prepared than others. One founder got so nervous that he had to turn the presentation over to his (more experienced) co-founder midway through. The investors preached preparation and simplicity in their feedback.

The best presentations defined the painpoint/problem clearly, addressed the market size, and stated their case as to why they’re the team to fix the problem. It sounds simple but keeping this clear and under seven minutes is quite a challenge.

Crowdtunes was probably the most polished presentation but they didn’t win and the judges feedback to them was telling. Crowdtunes’ major challenge will be distribution (getting into venues) and the investors wanted to hear more about how they would be addressing that obvious roadblock. Know your weaknesses and address them head on.

2.    To be a good investor, you have to see tons of pitches

There were a couple pitches that didn’t get me excited. My disinterest was founded in some combination of the market the startup was addressing, the founder’s lack of clarity, or my own lack of understanding. But for the companies that did get me excited (Crowdtunes, Rocketbolt, Fawn, Final Card), I found that I had very little context for evaluating these companies.

Savvy investors have a bank of previous pitches they use to compare ideas, market opportunities, and founding teams. While this comparison is inevitable, it remains probably the most helpful thing an investor could do. The same way a founder probably looks for successful startups to emulate, investors must need to see hundreds (if not thousands) of pitches to be able to discern which ideas, markets, and most importantly people, are worth investing in. 

 3.    Critically evaluating startups takes more than 7 minutes of slides and 3 minutes of questions

The pitches, even the best ones, are just a glimpse into the company. It’s impossible to know in ten total minutes whether or not you’ve found the next “unicorn.” On the panel of investors, each person had questions after every pitch and often the answers to initial questions necessitated further discussion. It’s clear why due diligence and spending time with founders is so essential to making an investment—with so many future unknowns, investors need to feel good about the basics behind the market, idea, and team.

4.    “Winning” a pitch event on its own means very little

Following the conclusion of all the pitches, the judges got together and picked a winner (so did the audience) with Final Card coming out on top in both sets of voting. On the one hand, this is a nice accomplishment. On the other, what does a win here get you? The answer is not much. Even in pitch competitions with money for the winner, it’s often not a ton (usually in the thousands of dollars). 

The benefit of these events is the exposure and potential connections. After the event I emailed Andrew Dietrich, Final Card’s founder, and volunteered a couple of connections that I thought would be useful for him. The fact that he “won” paled in comparison with the substance of what he’s working on. Ultimately, these events are a platform with the potential to be magnified and harnessed if done right.

5.    Duke has this whole network-with-alumni-in-startups thing figured out

Tech pulses through the veins of Silicon Valley and because seemingly everyone is in the industry, the chatter (dare I say Whisper?) regarding new companies is incessant and slightly insular. This very real geographic bubble creates an environment where everyone is looking for the latest and greatest company.

Given this, it’s ironic that the most talked about early stage startup of the past month (other than WhatsApp) is Secret. Secret is designed to let you be “authentic” and anonymous via social since the big boy social networks (Facebook, Twitter, LinkedIn, etc.) are now places to display our “best” identity. Secret’s product lets you view secrets posted by friends from your phonebook and leaves you guessing as to whose secret you’re actually reading. Since it launched in the App store January 30th, Secret has been making headlines — even rising all the way up to the number two spot in the social category without being featured by Apple.

I am not privy to the pitch that Secret founders Chrys Bader and David Byttow gave to their impressive list of investors (Kleiner Perkins, Google Ventures and a few more). There’s probably a much larger plan to flesh out their initial product into a full business or a service that provides a more significant value to consumers. But when people raise concerns about a reemerging tech bubble (not the geographical kind) this is the kind of company that worries me. No clear utility, a ton of hype, a likely forthcoming investment round at an inflated valuation. I’m biting my nails already.

I get the stickiness of it all — finding out your friend’s secrets is certainly addicting — but I put the product in the novelty category. Even Snapchat, Evan Spiegel’s hubris and all, has a clear utility: sending light and quick messages. But under what circumstances would I use Secret to do anything other than waste time? Maybe I’m too dull. Do I not have enough secrets?

Instead of incremental revenue growth as in most other sectors, tech startups often angle for massive adoption and figure out how to make money down the road. Even now publicly-traded Twitter (TWTR) is not yet profitable (I’m long on the stock/company). While this blueprint (if you can call it that) works for some startups, early adoption and usage still can’t always equate to lasting company value (see Foursquare).