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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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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

Do women that downplay their gender get ahead faster?

(OPINION) A new study about gender in the workplace is being perceived differently than we are viewing it – let’s discuss.

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The Harvard Business Review reports that women benefit professionally when they downplay their gender, as opposed to trying to focus on their “differences” as professional strength.

The article includes a lot of interesting concepts underneath its click-bait-y title. According to the study by Professors Ashley Martin and Katherine Phillips, women felt increasingly confident when they pivoted from focusing on highlighting potential differences in their perceived abilities based on their gender and instead gave their attention to cultivating qualities that are traditionally coded as male*.

Does this really mean that women need to “downplay” their gender? Does it really mean women who attempt this get ahead in this world faster?

I don’t think so.

The article seems to imply that “celebrating diversity” in workers is akin to giving femme-identified employees a hot pink briefcase – it actually calls attention to stereotyped behaviors. I would argue that this is not the case (and, for the record, rock a hot pink briefcase if you want to, that sounds pretty badass).

I believe that we should instead highlight the fact that this study shows the benefits that come when everyone expands preconceived notions of gender.

Dr. Martin and her interviewer touch on this when they discuss the difference between gender “awareness” and “blindness.” As Dr. Martin explains, “Gender blindness doesn’t mean that women should act more like men; it diminishes the idea that certain qualities are associated with men and women.”

It is the paradox of studies like this one that, in order to interrogate how noxious gendered beliefs are, researchers must create categories to place otherwise gender-neutral qualities and actions in, thus emphasizing the sort of stereotypes being investigated. Regardless, there is a silver lining here as said by Dr. Martin herself:

“[People] are not naturally better suited to different roles, and [people] aren’t better or worse at certain things.”

Regardless of a worker’s gender identity, they are capable of excelling at whatever their skills and talent help them to.

*Though the HBR article and study perpetuate a binary gender structure, for the purposes of our discussion in this article, I expand its “diversity” to include femme-identified individuals, nonbinary and trans workers, and anybody else that does not benefit from traditional notions of power that place cisgendered men at the top of the social totem pole.

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Opinion Editorials

Why I paused my career to raise our child

(OPINION) Our children are like tiny little sponges that absorb everything that we give them — your job and the sentiments it produces and evokes included.

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I never dreamed of being a stay-at-home-mom. Not in a million years did I think I’d find myself choosing to press pause on my career, but here I am, a mother for just nine months, doing just that.

HBR recently published an article about how our careers impact our children focusing on parental values and the emotional toll of our career involvement on our families. It got me thinking about my own childhood.

Growing up, my parents’ discussion of work was almost always negative. A job was something you had to do whether you liked it or not. As a child, I listened to my parents fight over money; I observed them in constant worry about the future. I watched them stress over unsatisfying jobs.

There was never any room for risk, no money to invest in a new career path, and no financial cushion to fall back on to give a new career time to grow.

Later, when choosing a path of my own, I would often wonder what my parents had wanted to be or who they could’ve been if they would’ve been able to choose careers they might’ve thrived in. All I ever knew is that my parents hated their jobs. While they’re on better financial footing now, the residue of their negativity persists in the career choices of their children.

While I was pregnant, I was working at an international tech startup in Silicon Valley. The company suffered from poor leadership; the week I was hired, my team quit and I was left to piece together a position for myself. The company continued to flounder, its culture unable to recover from interim toxic leadership.

I constantly worried about my son and the stress of a toxic culture on my pregnancy. Going into the office made me anxious. Leaving left me feeling stressed out and overwhelmed. Instead of imagining a bright, beautiful baby boy, I closed my eyes and saw a dark and anxious bundle of nerves. Of course, I blamed myself for everything.

Toward the end of my pregnancy, I promised my baby that when he arrived, I would do things differently. This would be the last time I accepted a job that I only felt lukewarm about. Never again would I participate in a culture that could diminish my talents and self-worth. I’d seen this kind of thing during my childhood and I’d be damned to repeat it.

During my career, I’ve watched coworkers hire full time live-in nannies, missing their baby’s developmental milestones and their children’s school events. I listened as one CMO talked about moving into his backyard yurt when the pains of parenthood became too much for him. He left his three preteen sons alone to fend for themselves in the mansion they shared in Silicon Valley.

We pride ourselves on the amount of work we put into our careers, but we rarely measure our success through the eyes of our children.

Children are mimics, they absorb everything we do, even during infancy. So, what are we offering them when we abandon them to make conference calls from yurts? What message are we sending them when our eyes are glued to texts, emails and push notifications? What are we teaching them when we come home stressed out, energy depleted and our values compromised?

We try “disrupting” anything these days so what about the working parent model? Would it be worth it?

My husband and I decided that it was and we’re doing things differently.

My husband works in the service industry. He doesn’t leave for work until late in the afternoon which means he spends all day with our son. At nine months old, my son has a strong emotional relationship with his father.

I carve out time during my days and nights to schedule writing work. I’ve recently returned to freelancing and I find that when I’m working with clients I believe in and doing work that I enjoy, we’re all much happier.

Everyone who’s ever had children says the first year goes by incredibly quickly. It’s true. My career will be there next year and for years after that. My son is only a baby once and I wouldn’t miss it for all the money in the world.

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Opinion Editorials

Zuckerberg makes eyeroll-worthy new years resolution

(EDITORIAL) This year, instead of losing weight, Zuckerberg is going to save himself and the world another way.

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Like the rest of us, Mark Zuckerberg, founder and CEO of Facebook, has announced New Year resolution – public talks on the future of technology in society. In a post on his personal profile page, he has pledged to participate in and host these discussions. Quite the step down from last year’s resolution to “fix Facebook.”

We get it, Mark, baby steps.

2018 saw Zuckerberg grilled by U.S. Congress and the European Parliament. His company suffered a drop in stock due to these hearings, was caught in the Cambridge Analytica firestorm and federal investigations, etc. It’s evident Zuckerberg bit off more than he could chew and his deciding to pull back isn’t surprising.

Here are the positives: the public needs more discourse on the future of tech and how it will affect the fabric of society. We want to connect with each other – we should pay more attention to what that truly means.

The entrepreneur titans leading the charge should be part of those discussions. Politicians, people elected to wield power for the public, are placed in debate situations regularly. Why shouldn’t the face of a global, digital platform be exempt from this basic practice?

If Zuckerberg is willing to truly have a candid talk (without prep or talking points), could we learn something new about his personal views? Does Officer Data have a soul after all?

But when all is said and done, talk is… just talk. The dangers with privacy on Facebook are already here.

The stakes are rising as the political and cultural landscapes are changing every year. It’s been two years since the problems with Facebook’s user information surfaced after the 2016 U.S. Presidential Election (and Ukraine actually blew the whistle in 2015). Zuckerberg has had quite a bit of time to reflect and “talk” about what needs to be done.

We try to keep to our resolutions every new year, and we’ll see if Zuckerberg can uphold his, or if his efforts disappear as quickly as my will to ween off my daily coffee routine. Even from a skeptic’s standpoint, I’ll eagerly wait to watch what goes down in this upcoming discussions.

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