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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

If you’re not constantly hustling, are you even living?

(EDITORIAL) If you aren’t hustling on the side, at night, while you eat, and in your sleep, are you really even a person in 2018?

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Back in the day, the idea of “hustling” was something of a negative concept (think Jon Voight and Dustin Hoffman in Midnight Cowboy). Now, if you’re not constantly hustling, and living that hustle life are you even living? If you don’t Rise and Grind, are you even a real person?

In this fast-paced, “I want it now” society, the assumption is that because we have 24 hours in a day, we must use every second of that time on one side hustle or another to make a few extra bucks, otherwise we’re not being productive. As Guru JP explains below, “being busy means you’re being productive. You do your best work when you’re always working. More quantity equals better quality.”

This has become one of the beliefs of entrepreneurialism: if you’re not working on your startup while Uber-ing at night and walking dogs via Wag on your lunchbreak, you’re not hustling and you’ll never be successful.

One important key of the hustle is to document how busy you are on social media, or else it’s not actually happening. Sharing a daily “rise and grind” pic on Instagram is the only way to appropriately start a manic day of hustle.

Despite what research would say, face-to-face communication is ineffective and computer mediated communication, or communication through text with no context or nonverbal cues, is the best way to relay messages. Also, if you’re hustling 24/7, there’s no way you have time for an in-person meeting when you’re on a FaceTime meeting while hosting a G-Chat team meeting simultaneously. I mean, come on.

The way that you know this is legit is that the hustle is referred to as a “game” which is how you should always describe your career path. Pople like volunteers in impoverished countries, single parents working ONLY two jobs, and people who built a business from the ground up and decided to only stay with that business, have no idea what hustling truly is (especially since none of it was documented on Snapchat).

And, the benefits of constant hustling are immense! You have unlimited time off and can take an unpaid vacation to anywhere in the world – just as long as there’s WiFi.

With hustling, you have so many options on how to make some extra scratch and start six different podcasts that all have a listener of one. Why wouldn’t you want to join this amazing idealism of entrepreneurship? Also, if you’re still reading, you’ve lost the game. Shouldn’t you be on to something else by now?!

Author’s note: In case you couldn’t tell, this entire article is incredibly facetious. Our COO wrote a popular editorial, rejecting the idea of hustling, and I completely agree with her on that. Constantly working to the point of exhaustion is, well, inefficient. Work on one thing, succeed, and then go from there. Ugh.

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Opinion Editorials

The strong case for Texas being technology’s next frontier

(EDITORIAL) Everyone loves Tacos and tech in Austin, but Texas has far more to offer – here’s how the various cities will create the next mecca for the tech world.

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texas capitol ceiling

Despite what the movies have told you, Texas is not the place you think it is. Sure, we’ve got cowboys, brisket, and a lot of BBQ, but the Lone Star State is much, much more than clichés. Over the last few decades, Texas has been gaining steam as one of the premier places to live in the country.

While yes, people love a good chicken fried steak or are always looking for an excuse to sneak over to their favorite grocery store, HEB, Texans aren’t sitting idly by when it comes to tech – they’re grabbing the industry by the horns.

Thanks to the state’s business-friendly tax breaks, a year-round predominantly warm weather climate, and a strong state culture, the popularity of Texas makes a lot of sense: Houston, which was once considered a third tier city is about to overthrow Chicago as the third largest in the nation, while also being lauded as our most diverse city.

Let’s repeat it, for all the people in the back: Houston, Texas is more diverse than Los Angeles, or New York.

Affordable neighborhoods are popping up across Houston, which are attracting immigrants from every culture looking for their slice of the American Dream. Houston is seeing explosive growth and a cultural shift away from being a town built on strictly fossil fuels, but now, startups, tech, and umbrella industries are finding their niche in the state’s biggest urban area. Only New York is home to more public companies.

Houston’s medical sector ranks with some of the top care in the world. And with those elite doctors, come the innovative pharmaceutical and medical companies, and the tech that supports them.

When you look at the top twenty metro areas to live right now in the country, four of those cities are in Texas. While some of those reasons are affordability and the signature Texas heat, the state is seeing new residents thanks also to a healthy job market. Since 2010, Texas has added 12.6% more residents, double lapping California’s growth of 6.1%.

Texas’ workforce is bigger than 46 states in the union total population and has doubled in job growth, productivity, and new deals are being struck daily. Texas’ impact on the tech sector is indisputable: Texas has exported more technology than California, again.

Deep in the heart

Startup culture is alive and well in Austin, but while some of our startups are finally beginning to draw VC attention away from Silicon Valley, we know how to slug it out in the land of the bootstrapped beginnings. If your company can thrive in Austin, with so many talented people, and a lot of great ideas, you can make it anywhere (sorry New York, for stealing your platitude).

Austin is still a developing story. As enterprises are opening offices in the capital city, this is helping VCs along the coasts see Austin’s potential as a hub of ideas. The city is still behind the bay area for risk-taking ventures, but given the current climate of investors, there’s a sea change happening.

Giants like Apple, Atlassian, Oracle, Dell, Amazon, Samsung, Facebook, and Google are all occupying space in buildings across the Austin skyline. Enterprise companies are investing heavily into the Austin market, and there are zero signs of a slow down. If you need further proof, just look at the traffic on any of the city’s major highways during rush hour.

Dallas is making a hard play at attracting the top-tiered companies as well. When Amazon head honcho Jeff Bezos announced put out a call for bids for Amazon’s HQ2, many cities made a play for the site, but now that the final cities have been chosen, both Austin and Dallas both stand to score the shopping monolith.

Oculus, TopGolf, and startups like Veryable, Dead Soxy, and Artist Uprising are attracting some of the brightest minds to the Dallas/Fort Worth metro area.

South Texas joins the party

San Antonio is quietly building a case for a burgeoning tech scene, too. It’s not quite there yet on the enterprise or startup level, but the city is widely known for one thing – cybersecurity. Outside of Washington D.C., San Antonio is known as “Cyber Security City USA” to folks in the black hat scene.

San Antonio logged the most substantial growth of all of the Texas cities, adding over 250,000 new residents in 2017 alone. Thanks to a robust military presence, San Antonio is quietly attracting more and more security-minded firms, a feat that’s unique in comparison to what the rest of the state is offering. Military-friendly banking institution USAA is headquartered in San Antonio, as is grocery chain HEB, and Whataburger, with all three companies investing heavily into user experience and mobile applications (aka technology).

If Amazon decides on HQ2 in either Dallas or Austin, that will signal a 200,000+ person addition to the state’s population and economy. That’s a lifetime investment into either city, wherever Bezos, and his board chooses. Coupling that possibility with the already strong presence of Southwest Airlines, Texas Instruments, and just about every major gas corporation, it’s easy to see why these moves are a huge deal. For the latter, it’s also important to note that every sector is bolstering their websites, their social media footprint, everything that can be done on a laptop is happening – one new job at a time.

As the tech scene develops and changes from a strong west coast-driven model, Texas is benefiting from the change. Many Californians are moving to Texas, which is an article to itself, but one thing remains: the Texas economy has never been stronger, and it’s only improving. The story of tech in Texas is a continual work in progress.

We’re not going to overtake California next year, but we’re making a stand, and people are noticing. If the current economic growth is an indicator, the famous Dairy Queen saying is potent with it’s accuracy: “That’s What I Like About Texas.”

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Opinion Editorials

How one podcast is giving a voice to veterans everywhere

(OPINION EDITORIAL) Veteran and former Paralympic skier begins volunteer podcast as a way to give voice to fellow veterans.

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veteran podcast h train

“Tough times don’t last, tough people do,” is the mantra that Joel Hunt lives his life by. As an Army veteran, who was injured during his third deployment, Hunt has seen his fair share of tough times.

After suffering a traumatic brain injury and partial paralyzation in his left leg, Hunt left the army and was in the care of his parents. They encouraged him to try Paralympic skiing as part of his rehabilitation.

While he was initially against the idea, he eventually warmed to it and wound up skiing in the 2014 Paralympics in Sochi, Russia. This accomplishment helped lead him to the path he’s on now, which is dedicated to helping fellow veterans.

Hunt is now the host of The H-Train Show, a podcast he produces in his Denver, Colorado home. His work on the podcast is done strictly through volunteering, and is dedicated to giving veterans a place to communicate.

“It’s something that helps keep me busy and makes me feel good,” says Hunt. “[It helps] to erase the past.” The podcast airs on Military Brotherhood Radio and has had a variety of guests – all dedicated to the significance of veterans.

In addition to the podcast, Hunt also assists veterans through organizations such as Project Sanctuary.

Hunt recently co-hosted an event with former Denver Broncos wide receiver, Brandon Stokley, that brought ten injured veterans to the Broncos training camp for a meet and greet. Accompanying Hunt at this event was his service dog, Barrett, who Hunt has taught to fold and do laundry.

Hunt explains that all of his efforts are dedicated to helping fellow veterans recover from the tragedies of war. While he says that, due to his brain injury, he does not recall deployment, he still carries the tragedies of losing fellow Army members.

Now, being retired both from combat and skiing, Hunt states, “My heart is to help other veterans avoid the fights for life I did. Not everyone can enjoy all the success I achieved, but at least I can help make the journey less of a struggle.”

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