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How I pitched the CEO of Reddit onstage at SXSW with no notice

(EDITORIAL) This is the story of how luck, networking, preparation and being at the right place at the right time got me onstage at SXSW with no notice, to pitch Steve Huffman, the CEO of Reddit and co-founder of Hipmunk.

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daniel senyard pitching the CEO of Reddit

After graduating from Austin’s Capital Factory accelerator earlier this year, Shep, my travel tech startup was in need of our first office. The team had grown to more than seven people, and while coffee shops had sufficed for product meetings when there were only four of us, we’d started getting dirty looks when we began putting tables together and colonizing entire corners. We looked at dedicated offices, office shares, and coworking spaces like WeWork. When it came down to it, at this phase, Capital Factory was the right choice for our company.

We’d already raised our seed round with Capital Factory with several of their partners as major investors, so we decided that, as a startup in Austin, we had to be where the press, investors, and partners were most likely to show up. Past visitors to Capital Factory have included Barack Obama, Apple CEO, Tim Cooke, Microsoft CEO, Satya Nadella, and many more. We knew that we might be able to get a space for less, but the community, education, and flow of people through the space optimizes our startup for serendipity.

Fast forward to this year’s SXSW and I was meeting with team members on the fifth floor when I received a text telling me that Steve Huffman, the CEO of Reddit and co-founder of travel startup Hipmunk, was downstairs and he had just said that creating a travel tech startup is the most difficult thing he’s ever done.

“The CEO of Reddit is talking right now and saying that doing a travel startup is the hardest thing he’s [e]ver done. You should tweet at him.” said the first text. “Baer just told him about Shep,” came the next one, referencing Josh Baer, the founder of Capital Factory, who was conducting the interview downstairs.

So, being in the right place (or at least four floors above) at the right time, I rushed downstairs and made eye contact with Josh before taking a seat in the back of the room. I planned to wait until after the talk and fight the crowd to introduce myself as the person Josh had mentioned and hand Steve a business card.

SXSW had other plans for me.

“So, we only have about three more minutes, and because SXSW is all about doing things on the fly and taking opportunity as it finds you, I’m going to ask Daniel Senyard from Shep, who’s just joined us, to come up and pitch Steve for 90 seconds,” said Josh from the stage before getting up and giving me his seat. I proceeded to tell Steve how Shep allows smaller businesses to set up and track travel policies and team spending on travel websites like Orbitz, Expedia, and Southwest through a free browser extension. My hands were shaking, but I got it all out in about the right amount of time, and he immediately responded by saying, “I love the Premise.”

Phew…

Steve asked some questions about customers (closed Beta) and target market (companies that spend less than $1M in annual travel) before enquiring whether Shep had to have relationships with online travel agencies (OTAs) like Expedia and Orbitz or Meta Searches like Kayak. I said no, but that through our strategic investors, I’d spoken to many of them.

“I’m trying to grill you, but I honestly think they would love this,” he said, stating how OTAs and other travel sites lose lots of bookings when companies grow and move from letting their team book on their favorite websites and instead mandate bookings be made on enterprise booking tools like Concur or AmEx Travel. Now Steve knows this world better than almost anyone, having co-founded an OTA that was actually acquired by the very company he says OTAs lose business to, Concur!

After a few more comments, I thanked him and took the opportunity to slip him a business card before heading back to my seat.

Now, to some, this may seem like pure luck but these moments of serendipity take years to create.

While there are several factors at play, it all essentially boils down to just showing up every time. As Josh said to me afterward, “Luck is when preparation meets opportunity,” and I’ve been preparing and pitching non-stop (albeit within three different businesses) for seven years. Over those seven years and three companies, I’ve slowly built up a vast network of connected people who will text me when my name is mentioned and will invite me onstage when they see an opportunity.

While I didn’t nail it, I didn’t flub my pitch because I’ve rehearsed various forms and lengths of pitches in mirrors, while driving, and to every family member that can stand it. I’ve taken my bumps and done my reps while probably pitching 200 times. I even won a contest and was sent over to Oslo to represent Texas at Oslo Innovation Week back in 2015. But even after pitching at every chance I’m given, I still get nervous, and my hands are still a little shaky while writing this, an hour after it all happened.

It was an amazing opportunity, and I’m very thankful to Henry for texting me, Josh for inviting me onstage, and John and Henry for recording the whole thing. While cool moments like this are certainly highlights, it’s just a step towards building brand recognition for our solution. Now I need to follow up and see if I can get Steve to join our advisory board…


Also read “Why your being the ‘Uber of’ or ‘Netflix of’ is bad for your business” by Daniel Senyard.

Daniel Senyard is a writer, speaker, serial entrepreneur and founder of travel startup, Shep . Over the course of seven years in the startup trenches, Senyard has done it all (fundraising, strategy, product management, marketing, band booking, photo-copying etc.). Born in South African, Senyard has lived in Africa, America, Europe and India, and has a funny accent.

Opinion Editorials

Culture can be defined by what employees don’t say

(OPINION) What your employees say defines your business. What your employees don’t say defines your culture.

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Whether the boss realizes or not, employees – the folks who often manufacture, handle, and sell the products themselves – can see sides of the business that management could easily overlook, including potential risks and improvements. So how do you make sure your employees are speaking up? A new study by Harvard researcher Hemant KakkarSubra Tangirala reveals that when it comes to speaking up, your company culture is probably either encouraging or discouraging it.

Tangirala wanted to compare two theories as to why employees choose to stay quiet when they could share their worries or ideas with company management. The “personality perspective” presumes that shy, reticent employees simply don’t have the gumption to speak up; therefore, the way to get more perspective from your employees is to make a point to hire extroverted people.

Meanwhile, the “situational perspective” posits that the company culture may either be encouraging and even expecting employees to speak up or discouraging it by creating an environment wherein employees “fear suffering significant social costs by challenging their bosses.”

In order to test these two theories against one another, Tangirala surveyed nearly 300 employees and 35 supervisors at a Malaysian manufacturing plant. First, the survey measured each employee’s “approach orientation,” that is whether or not, all things being equal, they had a personality more inclined to speaking up or staying mum. Next, employees were asked whether they thought their input was expected, rewarded, or punished. Lastly, supervisors were asked to rank the employees as to how often they spoke up on the shop floor.

The survey showed that both personality and the work environment significantly influenced whether or not an employee would speak up – however, it also showed that environmental factors could “override” employees’ natural inclinations. In other words, if employees felt that they were expected or would be rewarded for speaking up, they would do so, even if they aren’t naturally garrulous. On the other hand, even the most outspoken employees would bite their tongues if they thought they would be punished for giving their opinion.

The study also identified two major areas wherein employees could be either encouraged or discouraged from sharing their perspective. First, employees can be encouraged to suggest improvements or innovations that will increase workplace safety and efficiency. Secondly, employees should be expected to speak up when they witness dangers or behaviors that could “compromise safety or operations.”

Although the study was limited, it seems to point towards the importance of creating a workplace culture wherein your employees are rewarded for speaking up. Doing so could potentially provide you with invaluable insights into how to improve your business – insights that can only come from the shop floor.

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Opinion Editorials

How to change your negative mindset into something of value

(EDITORIAL) Once you’re an expert, it’s easy to get caught in the know-it-all-trap, but expertise and cynicism age like fine wine, and can actually benefit you/others if communicated effectively.

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mindset

In conversation with our friend John Steinmetz, he shared some thoughts with me that have really stuck with us.

He has expanded on these thoughts for you below, in his own words, and we truly believe that any individual can benefit from this perspective:

Over the last few years I have realized a few things about myself. I used to be trouble, always the dissenting opinion, always had to be on the opposite side of everyone else.

Then, I started reading everything I could get my hands on dealing with “how to change your attitude,” “how to be a better team player,” etc.

Over the course of that time I realized something. I realized that there was nothing wrong with me, only something wrong with how I communicate.

Unfortunately, once someone sets the context of who you are, they will never see you as anything else. I was labeled a troublemaker by those who didn’t want to “rock the boat” and that was that.

In my readings of books and articles by some of the most prominent technical leaders, they all had something in common. Paraphrasing of course, they all said “you can’t innovate and change the world by doing the same thing as everyone else.” So, in actuality, it wasn’t me, it was my communication style. For that reason, you have to say it out loud – “I will make waves.”

Physics

There are two things I reference in physics about making waves.

  • “A ship moving over the surface of undisturbed water sets up waves emanating from the bow and stern of the ship.”
  • “The steady transmission of a localized disturbance through an elastic medium is common to many forms of wave motion.”

You need motion to create waves. How big were the waves when the internet was created? Facebook? Just think about the natural world and there are examples everywhere that follow the innovation pattern.

You see it in the slow evolution of DNA and then, BAM, mutations disrupt the natural order and profoundly impact that change.

Communication

Where I was going wrong was, ironically, the focus of my career which is now Data. For those who do not know me, I am a product director, primarily in the analytics and data space.

More simply: For the data generated or consumed by an organization, I build products and services that leverage that data to generate revenue, directly or indirectly through the effectiveness of the same.

I was making the mistake of arguing without data because “I knew everything.” Sound familiar?

Another ironic thing about what I do is that if you work with data long enough, you realize you know nothing. You have educated guesses based on data that, if applied, give you a greater chance of determining the next step in the path.

To bring this full circle, arguing without data is like not knowing how to swim. You make waves, go nowhere and eventually sink. But add data to your arguments and you create inertia in some direction and you move forward (or backward, we will get to this in a min).

So, how do you argue effectively?

First, make sure that you actually care about the subject. Don’t get involved or create discussions if you don’t care about the impact.

As a product manager, when I speak to engineering, one of my favorite questions is “Why do I care?” That one question alone can have the most impact on an organization. If I am told there are business reasons for a certain decision and I don’t agree with the decision, let’s argue it out. Wait, what? You want to argue?

So, back to communication and understanding. “Argue” is one of those words with a bad connotation. When quite simply it could be defined as giving reasons or citing evidence in support of an idea, action, or theory, typically with the aim of persuading others to share one’s view.

Words matter

As many times as I have persuaded others to my point of view, I have been persuaded to change mine.

That is where my biggest change has occurred.

I now come into these situations with an open mind and data. If someone has a persuasive argument, I’m sold. It is now about the decision, not me. No pride.

Moving forward or backward is still progress (failure IS an option).

The common thought is that you have to always be perfect and always be moving forward. “Failure is not an option.”

When I hear that, I laugh inside because I consider myself a master of controlled failure. I have had the pleasure to work in some larger, more tech savvy companies and they all used controlled experimentation to make better, faster decisions.

Making waves is a way of engaging the business to step out of their comfort zone and some of the most impactful decisions are born from dissenting opinions. There is nothing wrong with going with the flow but the occasional idea that goes against the mainstream opinion can be enough to create innovation and understand your business.

And it is okay to be wrong.

I am sure many of you have heard Thomas Edison’s take on the effort to create the first lightbulb. He learned so much more from the failures than he did from success.

”I didn’t fail. I just found 2,000 ways not to make a lightbulb; I only needed to find one way to make it work.” – Thomas Edison

It is important to test what you think will not work. Those small failures can be more insightful, especially when you are dealing with human behaviors. Humans are unpredictable at the individual level but groups of humans can be great tools for understanding.

Don’t be afraid

Turn your negative behavior into something of value. Follow these steps and you will benefit.

  1. Reset the context of your behavior (apologize for previous interactions, miscommunications) and for the love of all that is holy, be positive.
  2. State your intentions to move forward and turn interactions into safe places of discussion.
  3. Learn to communicate alternative opinions and engage in conversation.
  4. Listen to alternative opinions with an open mind.
  5. Always be sure to provide evidence to back up your thoughts and suggestions.
  6. Rock the boat. Talk to more people. Be happy.
  7. A special thank you to John Steinmetz for sharing these thoughts with The American Genius audience.

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Opinion Editorials

Why tech companies should embrace Artist Residency Programs

(EDITORIAL) With technology founders wiping themselves with money while also truly caring about culture and inclusion, they’re missing a huge opportunity by ignoring artist in residency programs. Even Amtrak does it – come on, y’all.

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There’s a ton of cash in the tech industry. Like, more money than your primate brain can process, like “get-the-country-out-of-debt” money – Scrooge McDuck swimming in gold levels of cash. That’s how profitable technology has become.

And we’re not just talking laptops and smartphones, either. All of those monthly subscriptions you’re not thinking about, the Hulu, Netflix, Microsoft Office, that extra storage for your MacBook or iPhone, that’s all got a name: Software as a Service (SaaS) and with major players like Apple and Disney upping their stakes in the game – this model ain’t going anywhere.

Our thermostats are connected to our iPhones, and our cars are plugged into a matrix that’s fed into the Internet. Everywhere you look, the tech industry is changing everything. Everyone has a smartphone, a tablet, and a laptop, or a television that’s Internet-enabled.

And for everything that’s connected to the Internet, someone’s making a buck.

According to CTA, the tech industry will make $398B this year, and The Big 5 – Google, Apple, Amazon, Microsoft, and Facebook are worth a combined three trillion dollars. What do these companies do with all of the cash?

These companies typically pay well. To hire the best, workers want a payday. That’s fine, everyone who bangs at their job should get their slice of the action. After that, companies invest in culture and hiring that next tier of top talent. But, after the company offsites in a wooded cabin, the multi-million-dollar research projects, and the fully covered healthcare are accounted for, there’s still dough to play with.

Let’s get creative.

A lot of the more prominent tech companies have established that giving back is critical to their mission. Teams do charity work, they fly to other countries to help build schools; all kinds of amazing wonderful things are happening thanks to some of the world’s biggest players.

But what if those same companies established a new precedent – What if they established artist in residency programs?

One of the greatest professional experiences of my life was working for Atlassian and traveling between the Austin, San Francisco, and Sydney offices. While I was there to write for them, I’m still a writer, I always worked on my stuff. I’ve written in cafés in North Beach after browsing City Lights books where Ginsburg stomped his feet. I’ve been in bookstores in Sydney, never taking for granted for a second that I was beyond lucky to have this chance; that experience opened up a world that money had prevented me from exploring.

Can you imagine being allowed to fly to another office to work in a different environment, just for a change of scenery? It’s staggering what a comprehensive program could do for the arts community. The money and infrastructure is there, and so long as companies continue their dedication to paying it forward, this should be an added flavor to that mission.

This might sound like a shocker, but most of your friends who pursue art for a living ain’t exactly making windfalls of cash.

Most artistic types are freelancers or have multiple side hustles – they wait tables, or slug away in the bars, they cut corners on life’s everyday expenses in pursuit of their art. Your average painter, cartoonist, writer, filmmaker, they’re all chasing the project that gives them a chance to make their art their living. The problem is, for most creatives, it’s a dog chases its tail kinda life and that tail ain’t getting any longer or tastier.

How would it work?

Companies should work with the Alliance of Artist Communities (AAC) and set up a residency program. The AAC had been setting up residencies across the country for years, so while this is a feel-good philanthropic endeavor, the organization knows every tax break and loophole out there.

And realistically, the AAC has to, considering the culture of treating the arts in our communities is seen more of a begrudging, “we should probably do this” offense rather than an important investment. Most artistic programs receive pennies on the dollar, and most creatives live hand to mouth in pursuit of their dreams, and for many tech founders, the story is relatable, only they’re masters at problem-solving. Creativity doesn’t have to be pen to paper and the outcome being a funny doodle of a dog riding a skateboard, the creative mind is our innate core, we’re programmed to search for inventive ways to solve problems.

We just turn it off as society deems creativity an expendable commodity.

Creativity shouldn’t be relegated as frivolity, but essential.

In the world of artistic residences, paying bills is an issue. So, many programs have to drum up funds, find donors, seek out worthwhile endowments, search for tax breaks. Many are non-for-profits because they need grants for just about everything.

But in tech, cash is there aplenty.

Instead of throwing a Christmas party with a $100K budget for each office around the world, that money could be better spent on social enrichment. I’ve worked in the tech world for the past six years, and I’ve seen a lot of wasteful spending. While I love a good massage chair experience, that money could have been spent elsewhere versus giving staff of over three hundred already fabulously well paid people fifteen minutes of “me time.”

For one year or whatever predetermined amount of time, a company would allow a creative in their city to “join the team.”

What’s that look like?

Allow someone to create in these offices that are more like adult Disney World with their free snacks, open collaboration, catered meals, and endless perks. Give an artist a space that was once a small meeting room and let them do their thing.

The culture aspect of a creative being dropped in the average technology environment would blow their minds – most tech companies strive for diversity and inclusivity, and this program would be a brushstroke in that palette of reasoning.

By giving the creative the chance to mix it up with people who think in code, in marketing campaigns or how to “disrupt the market,” the influence would be impactful: a developer might become a nature photographer, or maybe a mixed media artist helps the marketing team see a problem from a different point of view. If there are anything companies in tech suffer from, it’s a little too much inward focus.

Change everything with a pen stroke.

Some campuses are so big (Facebook, Apple to name just two), they could support two or three artists at a time.

Indeed, Atlassian, Oracle, Uber, Lyft, all have multiple offices around the world. Imagine an extroverted painter working in a common room, while people move to and from meetings, getting that flash of inspiration, even if minute.

That’s beautiful.

Maybe instead of continually talking about code depositories or the next sprint, people got hip to new books? Maybe an essayist learns how to use Trello to manage their weekly pitches or maybe even further, they learn about how agile principles work could make their processes more manageable?

And while this person is getting paid, maybe they’re earning more money than they’ve ever seen. What if someone who’s always worked minimum wage jobs were given an $80K gig to create? Sure, you’d need to coach them on saving up for when the program is over, but for that period, being restricted to the dollar menu wouldn’t be everyday life.

The results would be staggering. The average working artist has to grind while others are asleep, early in the morning or late at night, they find ways to communicate their feelings, but while still making sure rent is on time.

Companies could establish an annual open competition where artists of whatever designated mediums submit their work.

Maybe it’s film or painting, or gosh, even a writer. But for that year, the winner gets to attend the fun parties, the culture building events, but most importantly gets paid well for their residency.

If the competition is opened up beyond the borders of the company’s home base, that works, too. Most bigger companies have a few corporate apartments that are barely used. Giving someone a room wouldn’t be that big of a deal.

Artists could donate their skills to workshops, creative programming, even create art specifically for the space. Most offices anywhere could use a little freshening up, or at least an ongoing blog series, something.

As for the perception of “selling out” the artistic culture has changed, where it was once punk rock to keep everything as DIY as possible, most of us creatives are fighting against a sea of other talented people all of the time, the chance for exposure on a bigger level, but also being financially free is worth wearing a few corporate branded t-shirts. And honestly, tech companies generally aren’t as gross as the old school monoliths of the past, most of the executive boards are made up of actual people who started from the bottom.

As my friend Jason Saul of BirdNote once told me, “don’t think of it as ‘selling out’ we’re in a hip hop-driven culture, you’re blowing up.”

There are residency programs on farms, a recycling center in SF, in the woods, the Florida keys, Amtrak got into the residency game for a while, just as Padre Island in Texas, the national parks all have them, even the CERN large hadron collider has an artist in residence program.

To double-down even further, even The Mall of America, the place where you can buy a corn dog or visit one of five Victoria’s Secret stores (who needs that many panties?) or ride a rollercoaster, has an artist in residence program.

The artist is given $2500 for a week, plus a hotel room and are allowed to roam the mall 24/7. LaGuardia airport in New York rehabbed an old Hudson News and converted it into a kiosk to people watch and create, so why not the tech companies who purposely set up shop in buildings in the heart of downtowns across the world or amongst trees in sprawling acreage?

This is possible.

Who’s going to be first?

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