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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.

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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

The measure of success is more than just salary

(EDITORIAL) Chicago-based hair stylist, Lindsey Olson, explains why passion and dedication is proven to be the most fruitful attributes for success.

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Six figure stigmas

For years, I’ve been interested in the societal stigma that you have to be a doctor or a lawyer in order to make a solid salary. But as time goes on, what I’ve learned is that it isn’t what you do that necessarily makes you money but what you put into it.

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We live in a different world today than we did even 20 years ago and we have more of an ability to think outside of the box when it comes to the search for success. Lindsey Olson, a Chicago-based hair stylist, is a living example of this.

Finding a passion and running with it

After developing an interest for hair early on in life, Olson began her career as a shampoo technician in a salon while still in high school. Immediately after graduation, she went into cosmetology school and continued bettering her craft.

Now, she has found success as a salon professional, as well as a Redken Exchange Artist and educator.

From there, it has become a matter of building onto the foundation of her success by trying new avenues and taking on new challenges.

Risk and reward

“I’ve always had the mindset that anything is possible,” says Olson. “It’s almost like taking risk. Once you start doing a little bit and see what happens, then you do a little bit more…the bigger the risk the bigger the reward. It really comes down to that if you believe in yourself, anything is possible.”

After her years working in a salon, Olson joined the Redken team in 2007.

With this, she has traveled internationally and has taught the ins and outs of hair coloring, cutting, and styling.

Being that the industry of style as a whole can be quite competitive, Olson has had to learn how to brand herself in a way that sets her apart from the competition. With this, she is very active on social media by sharing the work she has done with clients and models.

Branding against the competition

In addition, she also creates hair tutorials that she shares with her followers as a way to gain traction. “[What’s important is] making it known who I am as a person, as an educator, as a hair stylist, [sharing] my style and showing that to people,” Olson explains.

Despite the fact that her dentist tried to take the wind out of her sails in high school by asking what else she had lined up for herself besides cosmetology school, Olson has continued to take on bigger and better challenges. By doing shown, she has proven that a passion can be successful.

In Lindsey’s words

“Moral of the story, I think, is, don’t ever think that you can’t do something. The moments where you get to the place where you doubt yourself are almost some of the best,” states Olson. “If your life isn’t a little chaotic and challenging, you’re not living.”

#Redken

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Opinion Editorials

Why entrepreneurs need minimalism too

(EDITORIAL) You don’t have to ditch your couch and all but one cushion to be a minimalist. Try applying minimalist thinking to your job if you’re having trouble focusing.

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minimalism

As a concept, minimalism is often accepted as the “getting rid of most of your stuff and sleeping on the floor” fad.

In reality, minimalism is much closer to living an organized life with a pleasant sprinkling of simplicity as garnish—and it may be the answer to your entrepreneurial woes.

I in no way profess to be an expert on this topic, nor do I claim to have “all of the answers” (despite what 16-year-old Jack may have thought).

I’m a firm believer that you should take 99 percent of peoples’ suggestions with a grain of salt, and that mentality holds true here as well.

However, if you’re struggling to focus on your goals and you consistently fall short of your own expectations, following some of these guidelines may give you the clarity of mind that you need to continue.

First, reduce visual clutter.

If you’re anything like the stereotypical entrepreneur, you keep a thousand tabs open on your computer and your PC’s desktop is an unholy amalgam of productivity apps, photoshop templates, and—for some reason—three different versions of iTunes.

Your literal desktop doesn’t fare much better: it’s cluttered with notes, coffee rings, Styrofoam coffee cups, coffee mugs (you drink a lot of coffee, okay?), writing utensils, electronic devices, and…

Stop. You’re giving yourself virtual and visual ADHD.

Cut down on the amount of crap you have to look at and organize your stuff according to its importance. The less time you have to spend looking for the right tab or for your favorite notepad, the more time you’ll spend actually using it.

And, y’know, maybe invest in a thermos.

Instead of splitting your focus, try accomplishing one task before tackling another one.

You may find that focusing on one job until it’s finished and then moving on to the next item on your list improves both your productivity throughout the day and the quality with which each task is accomplished.

Who says you can’t have quality and quantity?

In addition to focusing on one thing at a time, you should be investing your energy in the things that actually matter. Don’t let the inevitabilities of adult life (e.g., taxes, paperwork, an acute awareness of your own mortality, etc.) draw your attention away from the “life” part of that equation.

Instead of worrying about how you’re going to accomplish X, Y, and/or Z at work tomorrow while you’re cooking dinner, try prioritizing the task at hand.

If you allow the important things in your life to hold more value than the ultimately less important stuff, you’ll start to treat it as such.Click To Tweet

Rather than stressing about the Mt. Everest that is your paperwork pile for the following Monday, get your car’s oil changed so that you have one less thing to think about.

Minimalism doesn’t have to be about ditching your 83 lamps and the football-themed TV stand in your living room – it’s about figuring out the few truly important aspects of your daily existence and focusing on them with everything you’ve got.

As an entrepreneur, you have the privilege of getting to do just that.

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Opinion Editorials

Two myths about business that could land you in a lawsuit

(EDITORIAL) Two misconceptions in the business world can either make or break a small business.

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Business casual

When you’re an entrepreneur with a small staff, you may be in the habit of running your team casually.

While there’s nothing wrong with creating a casual environment for your team (most people function better in a relaxed environment), it’s wise to pay close attention to certain legal details to make sure you’re covered.

Labor laws still apply

It’s easy to misinterpret certain aspects of labor law since there is a lot of misinformation about what you can and cannot do inside of an employee-employer relationship. And since labor laws vary from state to state, it can be even more confusing.

As an entrepreneur, it might be strange to think of yourself as an employer. But when you’re the boss, there’s no way around it.

Here are two employment myths you might face as an entrepreneur along with the information you need to discern what’s actually true. Because these myths carry a lot of risk to your business, it’s important that you contact an attorney for advice.

1. Employees can waive their meal breaks without compensation

It’s a common assumption that any agreement in writing is an enforceable, legally binding contract, no matter what it contains. And for the most part, that’s true.

However, there are certain rights that cannot be signed away so easily.

For example, many states in the US have strict regulations around when and how employees can forfeit their unpaid meal breaks.

While meal breaks aren’t required at the Federal level, they are mandated at the state level and each state has different requirements that must be followed by employers. While some states allow employees to waive their meal breaks, on the other end of that the employer is usually required to compensate the employee.

For example, in California an employee can waive their 30-minute unpaid meal break only if they do so in writing and their scheduled shift is no more than 6 hours. In other words, when a shift is more than 6 hours, the meal break cannot be waived.

Additionally, when an employee waives their unpaid meal break, they must be paid for an on duty meal break and be compensated with an extra hour of pay for the day.

Vermont, on the other hand, provides no specific provisions for meal breaks and according to the Department of Labor, “Employees are to be given ’reasonable opportunities’ during work periods to eat and use toilet facilities in order to protect the health and hygiene of the employee.”

As you can see, some states have specific regulations while others have general rules that can be interpreted differently by each employer. It’s best not to make any assumptions and contact a labor law attorney to help you determine exactly what laws apply to you.

2. You own the copyright to all employee works

So you’ve hired both an employee and an independent contractor to design some graphics for your website. You might assume you automatically own the copyright to those graphics. After all, if you paid money, shouldn’t you own it?

While you may have paid a small fortune for your graphics, you may not be the legal copyright holder.

Employees vs. independent contractors

When your employee creates a work (like graphic design) as part of their job, it’s automatically considered a “work made for hire,” which means you own the copyright. An independent contractor, however, is different.

While any legitimate work made for hire will give you the copyright, just because you created a work for hire agreement with your independent contractor doesn’t mean the work actually falls under the category of a work made for hire.

According to the Copyright Act (17 U.S.C. § 101) a work made for hire is defined as “a work specially ordered or commissioned for use as a contribution to a collective work, as a part of a motion picture or other audiovisual work, as a translation, as a supplementary work, as a compilation, as an instructional text, as a test, as answer material for a test, or as an atlas.”

This means that unless your graphic design work (or other work you paid for) meets these requirements, it’s not a work made for hire.

In order to obtain the copyright, you need to obtain a copyright transfer directly from the creator, even though you’ve already paid for the work.

Always play it safe

The boundaries of intellectual property rights can be confusing. You can protect your business by playing it safe and not making any assumptions before consulting an attorney to help you discern the specific laws in your state.

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