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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.

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Opinion Editorials

Follow these steps to change a 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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Man on couch drawing on ipad representative of change to the negative 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 or change.

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 negative 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.

A special thank you to John Steinmetz for sharing these thoughts with The American Genius audience.

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Opinion Editorials

Millennial jokes they let slide, but ‘Ok Boomer’ can get you fired

(EDITORIAL) The law says age-based clapbacks are illegal when aimed at some groups but not others. Pfft. Okay, Boomer.

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Boomer sad

A brand new meme is out and about, and it’s looking like it’ll have the staying power of ‘Fleek’ and ‘Yeet!’

Yessiree, ‘Okay, Boomer’ as related to exiting a go-nowhere conversation with out-of-pocket elders has legitimate sticky potential, but not everyone is as elated as I am. Yes, the Boomer generation themselves (and the pick-me’s in my age group who must have a CRAZY good Werther’s Original hookup), are pushing back against the latest multi-use hashtag, which was to be expected.

The same people happy to lump anyone born after 1975 in with kids born in 2005 as lazy, tech-obsessed, and entitled, were awfully quick to yell ‘SLUR’ at the latest turn of phrase, and I was happy to laugh at it.

But it turns out federal law is on their side when it comes to the workplace.

Because “Boomer” applies to folks now in their mid 50’s and up, workplace discrimination laws based on age can allow anyone feeling slighted by being referred to as such to retaliate with serious consequences.

However for “You Millenials…” no such protections exist. Age-based discrimination laws protect people over 40, not the other way around. That means all the ‘Whatever, kid’s a fresh 23-year-old graduate hire’ can expect from an office of folks in their 40s doesn’t carry any legal weight at the federal level.

And what’s really got my eyes rolling is the fact that the law here is so easy to skirt!

You’ve heard the sentiment behind #okayboomer before.

It’s the same one in: ‘Alright, sweetheart’ or ‘Okay hun’ or ‘Bless your heart.’

You could get across the same point by subbing in literally anything.

‘Okay, Boomer’ is now “Okay, Cheryl” or “Okay, khakis” or “Okay, Dad.”

You can’t do that with the n-word, the g-word (either of them), the c-word (any of them), and so on through the alphabet of horrible things you’re absolutely not to call people—despite the aunt you no longer speak to saying there’s a 1:1 comparison to be made.

Look, I’m not blind to age-based discrimination. It absolutely can be a problem on your team. Just because there aren’t a bunch of 30-somethings bullying a 65 year old in your immediate sphere doesn’t mean it isn’t happening somewhere, or that you can afford to discount it if that somewhere is right under your nose.

But dangit, if it’s between pulling out a PowerPoint to showcase how ‘pounding the pavement’ isn’t how you find digital jobs in large cities, dumping stacks of books showing how inflation, wages, and rents didn’t all rise at the same rate or defending not wanting or needing the latest Dr. Oz detox… don’t blame anyone for pulling a “classic lazy snowflake” move, dropping two words, and seeing their way out of being dumped on.

The short solution here is – don’t hire jerks – and it won’t be an issue. The longer-term solution is… just wait until we’re your age.

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Opinion Editorials

Decision-making when between procrastination and desperation

(EDITORIAL) Sometimes making a decision in business can loom so large over us that we delay making them until it’s absolutely necessary. Why?

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decision-making between procrastination and desperation

I need to confess something to you

So, a little confession’s good for the soul, right? I feel like I need to confess something to you, dear reader, before we jump right into this article. What follows is an article that I pitched to our editor some months back, and was approved then, but I’ve had the hardest time getting started. It’s not writer’s block, per se; I’ve written scores of other articles here since then, so I can’t use that as an excuse.

It’s become a bit of a punch line around the office, too; I was asked if I was delaying the article about knowing the sweet spot in decision making between procrastination and desperation as some sort of hipster meta joke.

Which would be funny, were it to be true, but it’s not. I just became wrapped up in thinking about where this article was headed and didn’t put words to paper. Until now.

Analysis by paralysis

“Thinking about something—thinking and thinking and thinking—without having an answer is when you get analysis by paralysis,” said St. Louis Cardinals pitcher Matt Bowman, speaking to Fangraphs.

“That’s what happened… I was trying to figure out what I was doing wrong, or if I was doing anything wrong. I had no idea.” It happens to us all: the decisions we have to make in business loom so large over us, that we delay making them until it’s absolutely necessary.

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Worse still are the times that we delay them until after such a time as when making the decision no longer matters because the opportunity or market’s already moved on. So we try to find the avenues for ourselves that will give us the answers we seek, and try to use those answers in a timely fashion. Jim Kaat, the former All-Star pitcher said it well: “If you think long, you think wrong.”

Dumpster Diving in Data

In making a decision, we’re provided an opportunity to answer three basic questions: What? So what? And now what?

The data that you use to inform your decision-making process should ideally help you answer the first two of those three questions. But where do you get it from, and how much is enough?

Like many of us, I’m a collector when it comes to decision making. The more data I get to inform my decision, and the sufficient time that I invest to analyze that data, I feel helps me make a better decision.

And while that sounds prudent, and no one would suggest the other alternative of making a decision without data or analysis would be better, it can lead to the pitfall of knowing how much is enough. When looking for data sources to inform your decision-making, it’s not necessarily quantity, but an appropriate blend between quantity and quality that will be most useful.

You don’t get brownie points for wading through a ton of data of marginal quality or from the most arcane places you can find them when you’re trying to make an informed decision. The results of your ultimate decision will speak for themselves.

“Effective people,” said Jack Welch, former CEO of General Electric, “know when to stop assessing and make a tough call, even without total information.”

Great. How do I do that?

So, by what factors should you include (and more importantly, exclude) data in your decision-making?

Your specific business sector will tell you which data sources most of your competitors use already, as well as the ones that your industry disruptors use to try to gain the edge on you.

Ideally, your data sources should be timely and meaningful to you. Using overly historical data, unless you’re needing that level of support for a trend line prediction, often falls into “That’s neat, but…” land. Also, if you’re wading into data sets that you don’t understand, find ways to either improve (and thus speed) your analysis of them, or find better data sources.

While you should be aware of outliers in the data sets, don’t become so enamored of them and the stories that they may tell that you base your decision-making process around the outlier, rather than the most likely scenarios.

And don’t fall into this trap

Another trap with data analysis is the temptation to find meaning where it may not exist. Anyone who’s been through a statistics class is familiar with the axiom correlation doesn’t imply causation. But it’s oh so tempting, isn’t it? To find those patterns where no one saw them before?

There’s nothing wrong with doing your homework and finding real connections, but relying on two data points and then creating the story of their interconnectedness in the vacuum will lead you astray.

Such artificial causations are humorous to see; Tyler Vigen’s work highlights many of them.

My personal favorite is the “correlation” between the U.S. per capita consumption of cheese and people who died after becoming entangled in their bed sheets. Funny, but unrelated.

So, as you gather information, be certain that you can support your action or non-action with recent, accurate, and relevant data, and gather enough to be thorough, but not so enamored of the details that you start to drown in the collection phase.

Trust issues

For many of us, delegation is an opportunity for growth. General Robert E. Lee had many generals under his command during the American Civil War, but none was so beloved to him as Stonewall Jackson.

Upon Jackson’s death in 1863, Lee commented that Jackson had lost his left arm, but that he, Lee, had lost his right. Part of this affection for Jackson was the ability to trust that Jackson would faithfully carry out Lee’s orders. In preparing for the Battle of Chancellorsville, Jackson approached Lee with a plan for battle:

Lee, Jackson’s boss, opened the conversation: “What do you propose to do?”

Jackson, who was well prepared for the conversation based on his scout’s reports, replied. “I propose to go right around there,” tracing the line on the map between them.

“How many troops will you take?” Lee queried.

“My whole command,” said Jackson.

“What will you leave me here with?” asked Lee.

Jackson responded with the names of the divisions he was leaving behind. Lee paused for a moment, but just a moment, before replying, “Well, go ahead.”

And after three questions in the span of less than five minutes, over 30,000 men were moved towards battle.

The takeaway is that Lee trusted Jackson implicitly. It wasn’t a blind trust that Lee had; Jackson had earned it by his preparation and execution, time after time. Lee didn’t see Jackson as perfect, either. He knew the shortcomings that he had and worked to hone his talents towards making sure those shortcomings were minimized.

Making trust pay off for you

We all deserve to have people around us in the workplace that we can develop into such a trust. When making decisions, large or small, having colleagues that you can rely on to let you know the reality of the situation, provide a valuable alternative perspective, or ask questions that let you know the idea needs more deliberation are invaluable assets.

Finding and cultivating those relationships is a deliberate choice and one that needs considerable and constant investments in your human capital to keep.Click To Tweet

Chris Oberbeck at Entrepreneur identifies five keys to making that investment in trust pay off for you: make authentic connections with those in your employ and on your team, make promises to your staff sparingly, and keep every one of them that you make, set clear expectations about behaviors, communication, and output, be vulnerable enough to say “I don’t know” and professional enough to then find the right answers, and invest your trust in your employees first, so that they feel comfortable reciprocating.

Beyond developing a relationship of trust between those who work alongside you, let’s talk about trusting yourself.

For many, the paralysis of analysis comes not from their perceived lack of data, but their lack of confidence in themselves to make the right decision. “If I choose incorrectly,” they think, “it’s possible that I might ________.” Everyone’s blank is different.

For some, it’s a fear of criticism, either due or undue. For others, it’s a fear of failure and what that may mean. Even in the face of compelling research about the power of a growth mindset, in which mistakes and shortcomings can be seen as opportunities for improvement rather than labels of failure, it’s not uncommon for many of us to have those “tapes” in our head, set to autoplay upon a miscue, that remind us that we’ve failed and how that labels us.

“Risk” isn’t just a board game

An uncomfortable fact of life is that, in business, you can do everything right, and yet still fail. All of the research can come back, the trend lines of data suggest the appropriate course of action, your team can bless the decision, and you feel comfortable with it, so action is taken! And it doesn’t work at all. A perfect example of this is the abject failure of New Coke to be accepted by the consumer in 1985.

Not only was it a failure to revive lagging sales, but public outrage was so vehement that the company was forced to backtrack and recall the product from the market. Sometimes things just don’t work out the way they’re supposed to.

You have to be comfortable with your corporate and individual levels of risk when making a decision and taking action. How much risk and how much failure costs you, both in fiscal and emotional terms, is a uniquely personal decision, suited to your circumstances and your predilections. It’s also likely a varying level, too; some decisions are more critical to success and the perceptions of success than others, and will likely cause you more pause than the small decisions we make day-to-day.

In the end, success and failure hinge on the smallest of factors at times, and the temptation is to slow down the decision making process to ensure that nothing’s left to chance.

Go too slowly, however, and you’ve become the captain of a rudderless ship, left aimlessly to float, with decisions never coming, or coming far too late to meet the needs of the market, much less be innovative. Collect the information, work with your team to figure out what it means, and answer the third question of the series (the “what”) by taking action.

#TakeAction

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