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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

How Gen X is nailing the COVID-19 social distancing order

(EDITORIAL) Of course, someone found a way to bring up generational stereotyping during COVID-19 and claim who is best, but are they onto something?

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Demographics and categorizing people helps us to process groups. A huge part of demographics and how we market ourselves in a job search, for example, is sharing our level of experiences and skill sets related to our profession – thus alluding to our age. Millennials (b. 1981-1996) received a lot of generational shame for being elitist and growing up in a time where they all received participation trophies – therefore being judged for not always winning a fair competition.

Gen X (roughly b. 1961-1981) has often commented that they feel like the forgotten generation which so much attention being play to the Baby Boomers (b. 1946-1964) who seemed to be born in to a great time of prosperity for “The American Dream” and then the Millennials who overtook Gen X and some of their jobs while they weren’t enough Gen Xers to fill them.

In this article “It Took a Global Pandemic, But Generation X is Finally Getting Love”, it is discussed how great Gen X is at this social distancing thing and maybe this will be helpful to anyone who feels like they are losing their mind. This is by no means an intent to shame any generation nor claim no one else knows how to handle it but this article does a great job about why Gen X might be primed to be handling the global pandemic well with the times they were raised in.

Right now, it’s a waiting game for many people who’s professions and lives have changed in what seemed like overnight. The patience required. The uncertainty of it all. The global pandemic forced (without any forgiveness), a swift move to new ways of life. The busy-ness of our days came to a crashing halt when we were no longer allowed to be out and about in places with large groups and possibly sent home to work remotely.

Many non-essential businesses were forced to close which meant people could not only not work at the office, but also had to cease their extra-curricular activities like working out at the gym, shopping, eating brunch with friends or taking their kids to their sporting events, a playground and/or coordinating a play date or sleepover. The directive from our local and federal government was for “social distancing” before the shelter in place orders came.

Gen X may agree that there were some pretty great things about their childhood – the types of things you do with your time because you don’t have a smartphone or tablet addiction and the fact that there was no way for your work to get a hold of you 24/7. Gen X did have TV and video games and sure, Mom and Dad didn’t really want you spending all of your time behind a screen but it also seemed that there wasn’t as much of a guilt trip if you did spend some of your “summer vacation” from school playing Nintendo or Sega with your neighborhood friends.

It seems like the article alludes to the idea that COVID might be helping people to get back to some of those basics before smartphones became as important to us as one of our limbs.

Gen X has had no problem adapting to technology and in their careers, they have had to adapt to many new ways of doing things (remember when caller ID came out and it was no longer a surprise who was calling?! Whaaaat?! And you can’t prank call anyone any more with your teenage friends at a sleepover! Gasp! You also wouldn’t dare TP an ex-boyfriend’s house right now).

Regardless of the need to learn new hard skills and technologies, everyone has been forced to adjust their soft skills like how technology and still being a human can play well together (since it is really nice to be able to FaceTime with loved ones far away). It seems those slightly unquantifiable adaptable and flexible skills are even more required now. It also seems that as you grow in your career, Emotional Intelligence might be your best skill in these uncertain times.

And not that we are recommending eating like crap or too many unhealthy items, Gen X has been known to be content surviving on Pop Tarts, Spaghetti O’s, Ding-dongs and macaroni and cheese which are all pretty shelf stable items right now. Whatever way is possible for you, it might be a good time to find the balance again in work, technology, home, rest, relaxation and education if at all possible.

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Opinion Editorials

How strong leaders use times of crises to improve their company’s future

(EDITORIAL) We’re weeks into the COVID-19 crisis, and some leaders are fumbling through it, while others are quietly safeguarding their company’s future.

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Anthony J. Algmin is the Founder and CEO of Algmin Data Leadership, a company helping business and technology leaders transform their future with data, and author of a new book on data leadership. We asked for his insights on how a strong leader can see their teams, their companies, their people through this global pandemic (and other crises in the future). The following are his own words:

Managers sometimes forget that the people we lead have lives outside of the office. This is true always, but is amplified when a crisis like COVID-19 occurs. We need to remember that our job is to serve our teams, to help them be as aligned and productive as possible in the short and long terms. 
 
Crises are exactly when we need to think about what they might be going through, and realize that the partnership we have with our employees is more than a transaction. If we’ve ever asked our people to make sacrifices, like working over a weekend without extra pay, we should be thinking first about how we can support them through the tough times. When we do right by people when they really need it, they will run through walls again for our organizations when things return to normal.

Let them know it’s okay to breathe and talk about it. In a situation like COVID-19 where everything is disrupted and people are now adjusting to things like working from home, it is naturally going to be difficult and frustrating.
 
The best advice is to encourage people to turn off the TV and stop frequently checking the news websites. As fast as news is happening, it will not make a difference in what we can control ourselves. Right now most of us know what our day will look like, and nothing that comes out in the news is going to materially change it. If we avoid the noisy inputs, we’ll be much better able to focus and get our brains to stop spinning on things we can’t control.
 
And this may be the only time I would advocate for more meetings. If you don’t have at least a daily standup with your team, you should. And encourage everyone to have a video-enabled setup if at all possible. We may not be able to be in the same room, but the sense of engagement with video is much greater than audio-only calls.
 
We also risk spiraling if we think too much about how our companies are struggling, or if our teams cannot achieve what our organizations need to be successful. It’s like the difference in sports between practice and the big game. Normal times are when we game plan, we strategize, and work on our fundamentals. Crises are the time to focus and leave it all on the field.
 
That said, do not fail to observe and note what works well and where you struggle. If you had problems with data quality or inefficient processes before the crisis, you are not fixing them now. Pull out the duct tape and find a way through it. But later, when the crisis subsides, learn from the experience and get better for next time.

Find a hobby. Anything you can do to clear your head and separate work from the other considerations in your life. We may feel like the weight of the world is on our shoulders, and without a pressure release we will not be able to sustain this level of stress and remain as productive as our teams, businesses, and families need us.

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Opinion Editorials

I just got furloughed. Now what?

(EDITORIAL) Some companies are furloughing employees, betting on their company’s long-term recovery. Here’s what you can expect and should plan for in your furlough.

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furloughed woman

Are you furloughed? You are not alone! What now? What does “furlough” even mean? How will I get money? Will I still keep my insurance?

A furlough differs from a layoff in a few ways. Whereas a layoff means you are definitely unemployed, a furlough is at its core unpaid time off. Not all furloughs are created equal, though the basic concept is the same: to keep valued employees on ice without being on the hook for their pay until a financial turnaround occurs.

The good-ish news is that a furlough means the company wants to keep you available. When a company is unable to pay their employees for an extended (often indefinite, as is the case with COVID-19 closures) period, they may opt to furlough them instead of laying them off. This virus has decimated whole industries, at least temporarily.

Furloughed employees are forbidden by law to do so much as answer a work email or text while furloughed–or else the company must pay them. The first large waves of COVID-19 furloughs are in obvious sectors such as hospitality (Marriott International), airlines industries (Virgin Atlantic), though other industries are following suit with furloughs or layoffs.

Some furloughs may mean cutting employees’ hours/days to a minimum. Maybe you’re being asked to take off a couple days/week unpaid if you’re hourly, or one week/month off if you’re on salary. With the COVID-19 situation, though, many companies are furloughing bunches of employees by asking them not to work at all. This particular furlough will last ostensibly for a few months, or until business begins to bounce back, along with normal life.

So, what are your rights? Why would you wait for the company? Can you claim unemployment benefits? What about your other work benefits? I’d be lying if I said I knew all the answers, as the furlough packages differ from company to company, and the laws differ from state to state.

However, here are some broad truths about furloughs that should apply. I hope this information helps you sort through your options. I feel your pain, truly. It’s a tough time all around. I’m on your side.

The first answer people want to know is yes, if you’re furloughed and have lost all or most of your income, you may apply for unemployment benefits. You can’t be expected to live off of thin air. Apply IMMEDIATELY, as there is normally a one or two week wait period until the first check comes in. Don’t delay. Some states provide more livable unemployment benefits (I’m looking at you, Massachusetts) than others, but some income is better than none.

Also, most furloughed employees will likely continue to receive benefits. Typically, life and health insurance remain intact throughout the length of the furlough. This is one of the ways companies let their employees know they are serious about wanting them back as soon as it’s financially realistic. Yet some other benefits, like a matching 401k contribution, will go away, as without a paycheck, there are no contributions to match.

Should you look for a job in the interim? Can you really afford not to? What if the company goes belly up while you’re waiting? Nobody wants that to happen, but the reality is that it might.

If you absolutely love your job and the company you work for and feel fairly confident the furlough is truly short-lived, then look for a short-term job. Thousands upon thousands of positions have opened up to meet the needs of the COVID-19 economy, at grocery stores or Amazon, for example. You could also look for contract work. That way, when your company reopens the doors, you can return to your position while finishing off the contract work on the side.

If the company was on shaky ground to begin with, keep that in mind when applying to new jobs. A full-time, long-term position may serve you better. At the end of this global health and economic crisis, some industries will be slower to return to their former glory–if they ever do. If you’re furloughed from such an industry, you may want to shift to something else completely. Pivot, as they say. Now would be a good time.

The only exceptions are “Excepted” government workers in essential positions, including public health and safety. They would have to work while furloughed in case of a government shutdown (and did previously).

Furloughs are scary, but they offer a greater measure of security than a layoff. They mean the company plans on returning to a good financial situation, which is encouraging. Furloughs also generally offer the comfort–and necessity–of insurance, which means you can breathe a bit easier while deciding your next move.

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