Boston Speaks Up (BSU) is a podcast owned and operated by Value Creation Labs. Listen to BSU on any podcast platform you choose: SoundCloud, Spotify, Apple Podcasts, Stitcher, and Google Play.
Jordan Staab is the CEO of SmarterTravel, an industry leader in online travel with a travel media portfolio including Airfarewatchdog, BookingBuddy, Family Vacation Critic, Oyster, SmarterTravel, and WhatToPack. As the story goes with most entrepreneurial ventures, Staab’s journey in building SmarterTravel endured various pivots, twists and turns to get to where it is today. The company is flourishing but Staab will be the first to tell you that this was not always the case.
With Staab at the helm, SmarterTravel empowers 7 million unique travelers each month through engaging content, innovative technology, and strategic partnerships to help them find the right trip at the right price. The company’s success was rewarded in September 2021 with a $9.5 million series B funding round co-led by Link Ventures and Second Alpha.
Staab was previously the VP of Revenue at Cognius, and later became CRO when it spun out of Link Ventures’ incubator CogoLabs. When Jordan saw that Cognius was able to predict patterns in travel consumer behavior, Staab co-founded Hopjump. That company started out in 2018 as a digital marketing agency that focused on partnering with brands to develop user acquisition campaigns. Staab and his team went on to launch their first product in January 2020 and saw 60,000 members join in the first few months. Staab was on a joyride that seemingly had no end, then the COVID-19 global pandemic took the world by storm and brought so much momentum, potential, and belief to an immediate halt.
Staab, along with the entire population, had one option, and one option only, PIVOT. Hopjump paused their travel product and focused on content. Staab then learned through industry contacts that TripAdvisor was looking to sell a number of their travel properties, many of which he was familiar with. He saw this as an immense opportunity for Hopjump, and purchased all of the properties, one of which was SmarterTravel. Since that name closely aligned with Hopjump’s purpose and goals, the company adopted that name and in September of 2021, announced funding and Staab’s bump to CEO.
A global pandemic was nowhere to be found in Staab’s playbook, but rest assured staying agile and nimble to whatever life throws at him, surely was. Find out how Staab not only stayed afloat, but flourished in one of the most challenging times the industry has ever seen in this week’s episode.
You can listen to our podcast discussion embedded below or on any podcast platform you prefer (SoundCloud, Spotify, Apple Podcasts, Stitcher, and Google Play):
Pre-podcast Q&A
Where did you grow up?
Charlotte, NC
What was your childhood like? Any early entrepreneurial ventures?
Awesome childhood, grew up in great neighborhood where we could ride our bikes to each other’s houses, and had a neighborhood pool that we lived at during the summer.
Worked at my uncle’s business many summers when I was early teens and learned a lot through exposure to all of the problems small businesses face. He owned a few businesses that sold and serviced high end medical equipment like xray, ultrasound, and nuclear cameras for hospitals. He never hid any problems from me and let me be in the room as much as possible to learn.
I started a pressure washing business in my teens that did pretty well, but only ran that for a summer. Fun to start from scratch though and just post flyers and land clients at a young age.
Also started a small business in college that was a nightlife website that bars and clubs could advertise on. I would send photographers to the bars to take pictures of people, and would post them on our site and hand out business cards to them to come to the site and check it out. This was pre camera phones, so sounds like a dumb business 15 years later, but it did pretty well and more importantly made sure I never paid for a beer out at bars!
What was the first career you remember wanting to pursue?
Sports medicine. I had an amazing teacher in high school and her class was actual athletic training, where we had to help rehab athletes and often were hands on at sporting events patching athletes back up. It was a sport in itself and it was a blast.
Next one was professional poker. I played way too much in college (which probably ended up being the most valuable ‘class’ I took).
Who were your role models growing up?
My parents, and my grandfather, and my peers. I never really thought anyone was perfect and that I wanted to be exactly like someone, but I always liked observing the traits they had that were amazing. My mom’s intelligence, kindness, brilliant problem solving, and patience. My dad’s work ethic and charisma, and control of every room he stepped into. My grandfather for an incomparable work ethic. My peers for brave kindness and choosing options that were counter to peer pressure in the awful experience that is being a teenager.
I think everyone is amazing at something, and can teach you something if you have the patience to listen.
Where did you go to college and what was your first job upon graduating?
UNC Chapel Hill. My first job was Dealer Services Rep at Evergreen Investments. Took the first job I interviewed for, and it was a great choice, learned a ton very quickly and made great friends that I still stay in touch with that are doing great things in Boston.
What’s the biggest lesson you took away from your time working in the consultancy space?
Prospective. The more problems you solve from many different industries and angles, the more you realize most problems are very similar. I also was running a company when I was 24/25 and looked like a child… so that helped get over a lot of insecurities early in my career. It was important to learn that the person judging you the most in almost every scenario is you. If you are talented, kind and genuine, that is all people care about, trust your abilities and never overcompensate.
What were you feeling in March 2020? Reflecting on one of the most challenging years of all of our lives, and debately the worst year the travel industry has ever seen, put us in your shoes when the pandemic hit in March 2020… What were you feeling? How did you keep going?
Privileged. Scary times, but very fortunate to have a job that we had the luxury of just going remote and didn’t break stride. Many people were not as fortunate and had a very difficult couple years.
From a business standpoint it was tough, we had to kill a product that was looking great, and on our agency side of the house we lost 70% of our clients in 2 weeks. We were able to pivot, rebuild and get back in the black in less than a month, then shifted into getting aggressive and doubled down in travel with our acquisition of smartertravel in July of 2020.
Now, let’s jump to the present day. How did the adversity that COVID brought to the world affect your team and make them stronger today than they were then?
I think it was empowering for our team to look back and see what they accomplished, and made them much more resilient to the inevitable challenges that are coming in the future.
How would you describe your leadership style?
Still learning here, I think it would be a combination of leading by example, and trying to empower my team as much as possible. I learned from making mistakes. I want to provide as much exposure and room for growth as possible because everyone I recruit is or will be smarter than me, and they usually just don’t have enough confidence in themselves yet.
What’s your advice to young founders?
Cliche, but ‘everyone is faking it,’ just trust yourself and go. I still fight the battle of trying to learn some magic formula that some other successful person used vs trusting that I know the right answer.
Your wife is also an entrepreneur and the founder of Scrappy Hats. As entrepreneurial parents, what message do you think this sends your kids as they grow into fine young adults and envision their own career paths?
I think we can talk about this one for a while on how you should definitely have a work life balance but providing your kids with visibility into strong work ethic and establishing the philosophy of if you want something just go do it, is really important as parents. They learn from what you do, not what you say.
What are you most excited about heading into the future -- personal or professional?
Personally, I am having a blast watching my kids grow up and I know it is cliche but I want it to slow down.
Professionally, uncharted territory for me, and I love solving new problems. We are building new products that I think can become household names over the next few years and that is really exciting.
What’s the biggest challenge facing the world you’d like to see addressed?
Classic heavy Zach question, haha…
Man, there are so many things that need to be fixed. When there are too many problems, I’m gonna take a somewhat boring answer and take a step back and look at improving our ability to solve those problems. I would like to increase the value of the generalist. We are becoming a very specialized society and the lack of perspective can be a huge weakness. Everything from our education to how we consume information is moving in a direction of specialization and siloes and people need to have exposure to other opinions and ideas to be able to solve that long list of problems that still exist in our society.
Throughout your career you’ve clearly demonstrated your immense drive for success which begs the question… What drives you to be the person you are? What is the legacy you want to leave behind for your children and the world?
I think I’m still trying to figure that out honestly, not sure if it is wanting to win, or not wanting to lose. But there is definitely a competitive component that is still growing.
I don’t like to not understand how something works… I remember in my 20s I needed to fix a hole in the wall at my apartment and realized that I had no idea how to fix it. I went on youtube and figured it out. I then needed to know how to build a house, so I took it to the extreme and bought a house, so I could gut it to the studs and rebuild it. Which I have done twice now, and love. I think that is a decent look into my personality.
FINAL QUESTION: We like the idea of ending our episodes with a challenge for the listeners/readers. Whether it be reaching out to an old friend, reading 5 pages a day from a book, starting a new podcast… what is one challenge you have for the listeners?
I think one of your earlier questions reminded me of how important your peers were to you when growing up, and I would challenge your audience to reach out to someone you grew up with that helped shape who you are today, and let them know. We don’t say thank you enough as a society, and trust me, you will make that person’s day.
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You can follow BSU on Twitter at @BostonSpeaksUp, and recommend BSU guests by contacting bostonspeaksup@gmail.com.