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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 truth about unemployment from someone who’s been through it

(EDITORIAL) Unemployment benefits aren’t what you thought they were. Here’s a first-hand experience and what you need to know.

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Have I ever told you how I owed the government over two grand because of unemployment in 2019, and only just finished paying it back this year?

This isn’t exactly the forum for memoirs, but this is relevant to everyone. So I’ll tell y’all anyway.

It all started back in 2018 when I came into work early, microwaved my breakfast, poured coffee, and got pulled into a collaboration room to hear, “We love you and your work, April, but we’ve been bought out and you’re being laid off.”

It was kind of awkward carrying my stuff out to the car with that Jimmy Dean sandwich in my mouth.

More awkward still was the nine months of unemployment I went through afterwards. Between the fully clothed shower crying, the stream of job denial, catering to people who carried rocks in their nostrils at my part-time job (yes, ew, yes, really), and almost dying of no-health-insurance-itis, I learned a lot!

The bigger lesson though, came in the spring of the following year when I filed my taxes. I should back up for a moment and take the time to let those of you unfamiliar with unemployment in Texas in on a few things that aren’t common knowledge.

1: You’re only eligible if you were laid off. Not if you had quit. Not fired. Your former company can also choose to challenge your eligibility for benefits if they didn’t like your face on the way out. So the only way you’re 100% guaranteed to get paid in (what the state calls) “a timely manner”, is a completely amicable split.

2: Overpayments have to go back. Immediately. If there’s an error, like several thousand of Texans found out this week, the government needs that cash back before you can access any more. If you’re not watching your bank account to make sure you’re getting the exact same check each time and you have an overpayment, rest assured that mistake isn’t going to take long to correct. Unfortunately, if you spent that money unknowingly–thought you got an ‘in these uncertain times’ kinder and gentler adjustment and have 0 income, you have a problem. Tying into Coronavirus nonsense is point three!

3: There are no sick days. If ever you’re unable to work for any reason, be it a car accident, childbirth, horrible internal infection (see also no-health-insurance-itis), you are legally required to report it, and you will not be paid for any days you were incapacitated. Personally, my no-health-insurance-itis came with a bad fever and bedrest order that axed me out of my part time job AND killed my unemployment benefits for the week I spent getting my internal organs to like me again. But as it turned out, the payment denial came at the right time because–

4: Unemployment benefits are finite. Even if you choose to lie on your request forms about how hard you’re searching for work, coasting is ill-advised because once the number the state allots you runs out…it’s out. Don’t lie on your request forms, by the way. In my case, since I got cut from my part-time gig, I got a call from the Texas Workforce Commission about why my hours were short. I was able to point out where I’d reported my sickness to them and to my employer, so my unpaid week rolled over to a later request date. I continued to get paid right up until my hiring date which was also EXACTLY when my benefits ran out.

Unemployment isn’t a career, which is odd considering the fact that unemployment payments are qualified by the government as income.

Ergo, fact number five…

5: Your benefits? They’re taxed.

That’s right, you will be TAXED for not having a job.

The stereotype of the ‘lazy unemployment collector burdening society’ should be fading pretty quickly for the hitherto uninformed about now.

To bring it back to my story, I’d completely forgotten that when I filed for unemployment in the first place, I’d asked for my taxes NOT to be withheld from it–assuming that I wasn’t going to be searching for full time work for very long. I figured “Well, I’ll have a tax refund coming since I’ll get work again no problem, it’ll cancel out.”

Except, it was a problem. Because of the nine month situation.

I’d completely forgotten about it by the time I threw myself into my new job, but after doing my taxes, triple checking the laws and what I’d signed, it was clear. Somehow…despite being at my lowest point in life, I owed the highest amount in taxes, somewhere around the 2k mark.

Despite being based on a system that’s tied to how much income you were getting before, and all the frustrating “safeguards” put in place to keep payments as low and infrequent as possible, Uncle Sam still wants a bite out of the gas-station Hostess pie that is your unemployment check. And as I’m writing this, more and more people are finding that out.

I’d like to end this on a more positive note…so let’s say we’ve all been positively educated! That’s a net gain, surely.

Keep your heads up, and masked.

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Opinion Editorials

COVID-19 acts are unfortunately too short sighted

(BUSINESS NEWS) The biggest flaw in the CARES act is simply that it won’t last. Numerous issues have extended the life of COVID-19 but the act hasn’t matched it.

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The CARES act gives an additional $600 weekly to those on unemployment assistance. The idea being that, combined with the $380 already granted by unemployment, the payments would roughly equal the wage of the average worker prior to the pandemic- about $1,000 weekly.

But on July 31st, the expansion that CARES provides will expire, and benefits will return to pre-pandemic amounts. Those currently receiving the maximum payment will see a 61% decrease in their income. In states that offer lower benefit payments, that percentage goes even higher. All of this comes during a national rental crisis, and moratoriums on evictions across the country are also nearing their ends or being extended last minute.

This isn’t the first or only “yuge” hole in the federal government’s COVID-19 safety net. Many Americans (this writer included) have seen neither hide nor hair of their promised stimulus checks. The HEROES act, which is being billed as a second round of stimulus money, remains under debate- as it has been for several weeks.

And the Families First Coronavirus Response Act, which requires certain businesses to provide two weeks of paid leave to workers who may be sick (or caring for someone who is) has plenty of problems too, namely the laundry list of exceptions to it.

This is just the most recent push to return to the pre-virus economy before effective protective measures have been put in place for workers and consumers alike. After all, with cases of COVID-19 spiking again in the US, it’s apparent that the act is still absolutely necessary. Our lawmakers either lack patience, or compassion – take your pick. Frankly, I say it’s both.

Not only have countless health experts warned that reopening too early will be disastrous, but if a second lockdown is in our future, all of the time, money, and human lives that went into reopening will be wasted.

There is a silver lining among the storm clouds on the horizon. Because ballooning unemployment has created long wait times for benefit applicants, unemployment assistance programs are shelling out retroactive back payments to those deemed eligible.

Good news, at least, for laid off workers who have been waiting months to hear their fate.

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Opinion Editorials

Women-owned businesses make up 42% of all businesses – heck yeah!

(EDITORIAL) Women-owned businesses make a huge impact on the U.S economy. They make up 42% of all businesses, outpace the national growth rate by 50%, and hire billions of workers.

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Women entrepreneurs make history in the U.S as female-owned businesses represent 42% of all businesses, while continuing to increase at DOUBLE the national growth rate!

Women are running the world, and we are here for it! The 2019 American Express State of Women-Owned Businesses Report, states 13 million women are now self-employed entrepreneurs. From 2014 to 2019, women-owned businesses grew 21%. Think that’s impressive? Well, businesses owned by women of color grew 43% within the same timeframe, with a growth rate of 50%, and currently account for 50% of all women-owned businesses! Way to go! What this also means is that women employ over 2.4 million workers who together generate $422.5 billion in revenue.

What can we learn from these women that’ll help you achieve success in your businesses?

  1. Get informed: In a male-dominated business industry, women are often at a disadvantage and face multiple biases. So, know your stuff; study, research, and when you think you know it all…dig deeper!
  2. Stay hungry: Remember why you started this journey. Write down notes and reminders, goals, and inspirations, hang them up and keep them close.
  3. Ask for advice: Life is not meant to go through alone, so ask questions. Find a mentor and talk to people who have walked a similar path. Learning from them will only benefit your business.

Many of these women found ways to use their passion to drive their business. It may not be exactly what they thought it would be when they started out, but is it ever? Everyone has to start off small and rejection is part of the process. In fact, stories of rejection often serve as inspiration and encouragement to soon-to-be self starters.

Did you know J.K Rowling’s “Harry Potter” book was turned down TWELVE times? Seven books later with over 400 million copies sold, the Harry Potter brand is currently valued at over 15 billion. While you might not become a wizard-writing fantasy legend like J.K Rowling, you sure as heck can be successful. So go for it, and chase your dreams.

If you want to support women-owned businesses, start by scrolling through Facebook or doing some research to find women-owned businesses in your community. Then, support by buying or helping to promote their products. Small businesses, especially women-owned, black women-owned, and women of color-owned, are disproportionally affected by the current economic crisis ignited by a health pandemic. So if you can, shop small and support local. And remember, there’s a girl (or more) doing a happy dance when you checkout!

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