Landon Vago-Hughes of YSplit: “Gratefulness”

Gratefulness: The successes are not just your successes and need to be shared. It is always we and never I because there would be no company without the team. When you get a new customer, this isn’t just sales it is sales, product, strategy, and customer success that have all worked together to make the […]

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Gratefulness: The successes are not just your successes and need to be shared. It is always we and never I because there would be no company without the team. When you get a new customer, this isn’t just sales it is sales, product, strategy, and customer success that have all worked together to make the product better for the next person.


Being a founder, entrepreneur, or business owner can have many exciting and thrilling moments. But it is also punctuated with periods of doubt, slump, and anxiety. So how does one successfully and healthily ride the highs and lows of Entrepreneurship? In this series, called “How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur” we are talking to successful entrepreneurs who can share stories from their experience.

I had the pleasure of interviewing Landon Vago-Hughes co-founder of YSplit, a fintech company based in NYC. Born in Greenwich, raised in Wimbledon, he attended the University of Southampton where he studied Mechanical Engineering. He did not however pursue this career. He taught himself how to code in college to pursue some ideas he wanted to make. He met some brilliant minds along the way and eventually joined forces with them to start YSplit. He then proceeded to get funding for YSplit from investors such as Paul Graham (co-founder of YC) and Paul Bucheit (Inventor of Gmail).


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

Sure, well before college, I didn’t know where I wanted to end up. Life was pretty standard for me. I attended the London Oratory School in the UK and then the University of Southampton.

My business side didn’t bloom until I was in college unless you count my side hustle of selling sweets in high school. Honestly, after high school, I thought I was going to be building either plane, rockets, or F1 cars. I knew the degree I wanted to pursue, but that was it.

College was where I found a passion for entrepreneurship. I had an idea, and then my next thought was, how do we make it?

Months and months of weekends spent at Hackathons helped me improve my coding abilities to the point where I was comfortable building something from scratch. All I needed was the idea and a team.

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

It was 2018, and we were building a productivity tool at the time. We had just received our YCombinator offer to attend the W19 batch.

We asked ourselves a simple question, do we want to be working on a rocket ship? Or work on a productivity tool for Roommates that had no business model?

In your opinion, were you a natural-born entrepreneur, or did you develop that aptitude later on? Can you explain what you mean?

I should ask my brother or mother this because maybe they’ll remember more about my youth than I did. I’ve had an aptitude and desire to make things.

However, to keep getting to make things, you have also to make money to support the project. Suddenly other people want to buy what you have, give you money to help you build more.

Becoming an entrepreneur is just a consequence of building something you love and wanting others to use it.

Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?

I didn’t honestly have any direct inspiration from anyone close to me. I do, however, want to thank my mother for not judging me for getting in my way. She was just super supportive.

Imagine your son saying I’m going to be unemployed for a couple of years working on this thing that has a low probability of working.

I respect any parent that lets their children make their own mistakes and decisions.

What do you think makes your company stand out? Can you share a story?

We are very fast at executing and learning from mistakes.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Focus: There are always a million things you could be worried about, but the most important things are your north star metrics: most likely revenue and churn rate. Everything else is a subset of this. Everything makes a lot more sense when looking at things like this.

Hard work: Nothing beats it. Most people give up on the first hurdle. The problems with the most significant rewards are the hardest to solve. If your business is complex and takes ten years to build, you’ve created a strong business. You’ll have such insight into the market that no one can touch you.

Inputs over outputs — It is more important to spend time executing something and thinking things over in detail than just to release something

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

Which tips would you recommend to your colleagues in your industry to help them create a work culture in which employees thrive and do not “burn out” or get overwhelmed?

As a startup, we know it is a marathon. So we don’t expect to work 14 hour days and advise our employees to do so also.

The most important thing is that everyone is working on the right thing and being productive with the time that they do have.

Are they trying to solve complex problems in their workday or defaulting to easy tasks?

This is why we regularly review the metrics with weekly cycles and standups so everyone can help each other out.

What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?

Be super transparent about how you are using personal data.

Can you help articulate why doing that is essential today?

We live in a time where data is the most valuable commodity, and your data is used for everything.

Facebook, Amazon, and Google are all being summoned to congress every month for data concerns causing people to worry about their data.

This led to GDPR in Europe. Now it is a sin not to be compliant.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

Not making something people want, not being passionate about the idea in the first place, and not focusing on revenue from day one.

I can kill two birds with one stone here. To find out if you are making something people want, ask them to pay for it. This is the best indicator.

Don’t make the product accessible. Set a price and see if people would want it. You are creating value and this is not charity. Unless you’re a social network, you need to charge for your product.

When it comes to being passionate, you can quickly think you are emotional, but really you just convinced yourself that this was something you wanted to work on without realizing the road ahead. For college kids, this is harder. You are passionate about many things.

However, you can ask yourself some simple questions to make sure this is something you want to be doing, such as do you want to be working on X for the next ten years? How long have you been interested in this field? How much do you already know about this field?

These questions can help you understand if this is where you want to head.

Ok fantastic. Thank you for those excellent insights, Let’s now shift to the main focus of our interview about How to Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur. The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. This might be intuitive, but I think it will be very useful to specifically articulate it. Can you describe to our readers why no matter how successful you are as an entrepreneur, you will always have fairly dramatic highs and lows? Particularly, can you help explain why this is different from someone with a “regular job”?

As a founder, we are constantly working on the biggest problems in the company.

You are the captain navigating the ship and dodging icebergs, while a regular sailor is typically just told what to do. So when you make a mistake, everybody notices and could wreck the company if you aren’t careful.

You are potentially the most accountable person in your company. So your lows are really low. Lower than any lows an employee could face.

Do you feel comfortable sharing a story from your own experience about how you felt unusually high and excited as a result of your business? We would love to hear it.

The first time seeing users sign up for our premium product was excellent.

This was scary for us because we were a free product before.

Do you feel comfortable sharing a story from your own experience about how you felt unusually low, and vulnerable as a result of your business? We would love to hear it.

As a founder, you know that you have to be growing week over week, and so when you are not, it sucks a lot.

We used to have ads running to get some initial users; however, we stopped them from seeing how we could grow in other ways i.e, through word of mouth, referrals etc, we suddenly stopped growing at the rate we wanted.

Based on your experience, can you tell us what you did to bounce back?

We learned that we could never rely on one growth mechanic. This helped us know to track all growth methods and continually grow in more than 1 area.

Ok super. Here is the main question of our interview. What are your “Five Things You Need To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur”? Please share a story or an example for each.

I’ll give 2 things for the highs and 3 for the lows.

  1. Modesty: Gloating is not a great trait to have. No one will want to share your highs. Those close to you will also not want to share anything with you out of fear you will judge them or overshadow them. This can lead to a lonely life.
  2. Gratefulness: The successes are not just your successes and need to be shared. It is always we and never I because there would be no company without the team. When you get a new customer, this isn’t just sales it is sales, product, strategy, and customer success that have all worked together to make the product better for the next person.
  3. Mentors — Whenever we get stuck on a problem, we call our YCombinator partners. This happens when things are going well but also badly. There is never judgment when we call our mentors, just facts and advice from previously successful founders.
  4. Therapy: Talking over issues with someone unbiased is amazing. They don’t know you at all. Their advice will be a lot more realistic than your friend, who also needs some therapy. I used Betterhelp occasionally when things start to feel overwhelming. I can lay it all out in front of me, and my therapist can help me ask the right questions to make sense of it.
  5. Exercise: This will release many endorphins into your body that will boost your mood naturally. If you are at a low point, exercise can bring you out.

We are living during challenging times and resilience is critical during times like these. How would you define resilience? What do you believe are the characteristics or traits of resilient people?

If you are a long-term thinker, this will help a lot.

You’ll see the light at the end of the tunnel. This will help you realize that it is worth continuing on this path.

I would think that leaving emotions behind is essential when being resilient. You have to be super logical when it comes to making decisions during times of uncertainty.

Did you have any experiences growing up that have contributed to building your resiliency? Would you mind sharing a story?

One that stands out was my dad leaving my mum while I was an early teen.

I had to keep my head up, go to school and finish exams.

There are probably more, but this one stood out, and I’m impressed I dealt with that event so well.

In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?

I try my best, but it is easier said than done.

I tell myself that there is an opportunity to learn if it is hard.

This is easier said than done, but there are many difficult situations along the startup journey, so you have to stay positive or not last long.

This isn’t to say I haven’t had my fair share of needing to scream into my pillow every so often or spend an hour meditating to get some space.

Can you help articulate why a leader’s positive attitude can have a positive impact both on their clients and their team? Please share a story or example if you can.

Well, you are a leader, so people look up to you.

If I looked at the plane’s pilot and looked scared or panicking, I would reflect the same emotions. The pilot knows how to fly the plane; no one else does, so you have to show face to everyone.

One can still be very confident and transparent when things are going wrong. Clients and team members will respect this behavior because they understand things go wrong sometimes.

Our users were, at some point, messaging us consistently about bugs we were trying to fix over a couple of days.

We could have lost many users during this period, but instead, we were super transparent and positive about fixing these issues. Our users had confidence in us.

Our positive and friendly attitude towards the situation made them feel empathy for us, not resentment and hatred.

Ok. Super. We are nearly done. What is your favorite inspirational quote that motivates you to pursue greatness? Can you share a story about how it was relevant to you in your own life?

If it was not hard, everyone would be doing it.

Simple and obvious but resonates with me.

Only when you are working on the most complex problems can you make real change in the world.

How can our readers further follow you online?

I’m on Tiktok sharing Startup advice, and I have a podcast where I share updates on my week with my cofounder as we build YSplit. We go through the ups and downs. Warts and all. It is called The Startup Diary.

This was very inspiring. Thank you so much for the time you spent with this. We wish you continued success and good health!

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