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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

The offensive myth of getting laid off being a blessing

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There’s an age-old trend in news to look for rags-to-riches stories. People love to hear about someone who’s down on their luck scraping together a genius idea and, through sheer grit (it seems), finding the motivation to finally strike out on their own and realize their dream.

Stop me if you’ve heard this one: Person X is laid off from their long-time but unfulfilling office job, say at an oil company in Alberta, or a marketing agency where their good ideas are consistently shot down.

What seems like a situation to for despair is actually an opportunity in disguise— see, with their newfound freedom Person X has the ability to fully commit to their small business pipe dream.

In fact, the story goes, getting laid off was actually the best thing to ever happen to this person.

This story is a myth.

Although I don’t want to discredit anybody who has had the willpower, luck, and resources to succeed at launching their business, there are many people who are laid off who are truly in critically terrible times.

The insidious underlying message of this myth is that anybody who is truly devastated by being laid off is being weak or lazy.

It serves to alleviate the guilt of those who may have survived the lay off themselves; it helps organizations justify the fact that they might have had to let an otherwise good employee go for their own, corporate-level problems.

The characteristics that many of these laid-off-turned-successful-entrepreneurs have in common are the same sort of privileges that many take for granted – health, youth, a personal support system to help keep the lights on, and an established network of people that can be turned into a market of clients.

What happens to the many workers who are victims of ageism when they are laid off in favor of younger, less expensive workers?

What happens if you’re laid off and you can’t use your newfound time to work on your business plan because you’re raising young children?

The entrepreneurs who find opportunity in being suddenly jobless were probably already on their way to striking out on their own, with their being laid off acting as the defined starting point for a plan they might not have known was forming in their heads.

If you, a friend, or a colleague have the unfortunate luck to be laid off, don’t let this myth get under your skin.

It’s okay to have a rough time with a huge life event that is absolutely terrifying and difficult.

Hang in there.

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Opinion Editorials

3 things to do if you *really* want to be an ally to women in tech

(EDITORIAL) Diversity is known to strengthen the overall performance of a company and its teams, and there are a number of ways you can be an ally to the talented women already on your workforce.

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More and more women are leaving their positions with tech companies, citing lack of opportunity for advancement, wage gaps and even hostile working conditions as some of the reasons why.

What’s better for the tech industry and its employees than cultivating inclusive and diverse departments? Diversity is known to strengthen the overall performance of a company and its teams, and there are a number of ways you can be an ally to the talented women already on your workforce. To name a few:

1. Be open to listening to different perspectives.

It can be awkward to hear so many reports of workplace politics stacking against women, especially if you’re not a woman!

Instead of getting uncomfortable or defensive – ask open ended questions and be interested in a perspective that isn’t yours and may be unfamiliar.

Don’t seek to rationalize or explain the experiences you’re hearing about, as that can come off as condescending. It’s common for women to be interrupted or spoken over in team gatherings. If you notice this happening, bring the conversation back to where the interruption began. Offering your ear and counting yourself as responsible for making space will improve the overall quality of communication in your company.

Listening to and validating what women have to say about the quality of their employment with a company is an important step in the right direction.

Expressing something as simple as “I was interested in what you had to say – could you elaborate on your thought?” can help.

2. Develop an Employee Resource Group (ERG) program.

An ERG is a volunteer-based, employee-led group that acts as a resource for a particular group of employees. An ERG can help to foster inclusiveness through discussion, team-building activities and events. It’s common for a department to have only one or two women on the roster.

This can mean that the day to day feels disconnected from concerns commonly shared by women. disjointed it might feel to be on a high performing team, without access to relatable conversations.

3. Be responsible for your company’s culture.

Chances are, your company already has some amazing cultural values in place. That said, how often are you checking your own performance and your co-workers performances against those high standards? Strong company culture and values sound great, but whether or not they’re adhered to can make or break the mood of a work environment.

Many women say they’ve experienced extremely damaging and toxic cultural environments, which lead to hostility, frustration, and even harassment. Take action when you see the new woman uncomfortable with being hit on at team drinks.

Call out those who make unfriendly and uncouth comments about how women perform, look, or behave.

Setting a personal threshold for these kinds of microaggressions can help you lead by example, and will help build a trustworthy allyship.

(This article was first published here in November, 2016.)

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Opinion Editorials

How the Bullet Journal method has been hijacked and twisted

(EDITORIAL) I’m a big fan of the Bullet Journal method, but sticker-loving tweens have hijacked the movement. Worry not, I’m still using black and white bullet points with work tasks (not “pet cat,” or “smile more”).

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bullet journal

It’s taken me some time to come around to the Bullet Journal method, because it took me some time to fully understand it (I have a tendency to overthink simplicity). Now that I understand the use, I find it very beneficial for my life and my appreciation for pen-to-paper.

In short, it’s a quick and simple system for organization tasks and staying focused with everything you have going on. All you need to employ this method is a journal with graph or dotted paper, and a pen. Easy.

However, there seems to be this odd truth that: we find ways to simplify complicated things, and we find ways to complicate simple things. The latter is exactly what’s happened with the Bullet Journal method, thanks to creative people who show the rest of us up.

To understand what I’m talking about, open up Instagram (or Pinterest, or even Google) and just search “bullet journal.” You’ll soon find post after post of frilly, sticker-filled, calligraphy-laden journal pages.

The simple method of writing down bullets of tasks has been hijacked to become a competitive art form.

Don’t get me wrong, I like looking at this stuff because I dig the creativity. But, do I have time to do that myself? No! For honesty’s sake, I’ve tried just for fun and it takes too much damn time.

With this is mind, this new-found method of Bullet Journaling as an art is something that: a) defeats the purpose of accomplishing tasks quickly as you’re setting yourself back with the nifty art, and b) entrepreneurs, freelancers, executives, or anyone busy would not have time for.

Most of these people posting artistic Bullet Journal pages on Instagram are younger and have more time on their hands (and if you want to spend your time doing that, do you, man).

But, it goes against the simplistic method of Bullet Journaling. The intent of the method.

And, beneath the washi tape, stickers, and different colored pens, usually lies a list of: put away laundry, feed cat, post on Insta. So, this is being done more for the sake of art than for employing the method.

Again, I’m all for art and for people following their passions and creativities, but it stands to reason that this should be something separate from the concept of Bullet Journaling, as it has become a caricature of the original method.

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