Balance. Try to have balance but also allow yourself to ditch that concept temporarily. People say it’s a marathon, not a sprint, but when you’re in a startup it feels like both. To keep yourself mentally, physically and emotionally able to run the race — focus on eating well, exercising, making time for friends and family and having downtime. That said, sometimes you’re in a crunch and you let that stuff go. Sometimes you’ll be so exhausted that you should give yourself permission to ditch the gym, and be anti-social for a while to just rest your body! We can’t do it all. But longer-term, the more balance you can keep, the better.
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 interviewingSarah Neill, CEO & Founder, Mys Tyler.
Sarah is a technology and startup powerhouse with over 15 years driving marketing and innovation for major consumer technology brands in the USA, UK and Australia.
Sarah has held senior leadership roles at mobile disruptors Boost Mobile and Mint Mobile, led multi-million-dollar agency accounts for marquee companies Vodafone and Samsung; and as a serial entrepreneur founded companies Doodad (raising more than 1 Million USD to disrupt the global roaming industry), A Relatively Unique Inc and Mys Tyler — a fashion tech company solving the 1 trillion dollars “fit” problem by creating an empowering, personalized shopping experience for women.
Sarah holds an MBA (International Business) from Griffith University, a Bachelor of Commerce (Marketing) from Macquarie University, and a Certificate in Disruptive Innovation from Harvard Business School.
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?
I started my career in marketing and advertising, working for both large agencies and on the client-side. In advertising, I learned how to dig into the target audience to understand what they think and what problems they have to solve, in order to communicate the solution in the most compelling way. While on the client-side, I had more of an opportunity to influence the actual product/ service to better meet customer needs. I really enjoyed this part of it, and over time as I better understood the problems that existed, I started coming up with ideas for new products and services myself. This is how I started my entrepreneurial journey. In 2012, while I was living in New York working for a telecommunications company, I pitched one of my ideas to the owner. Rather than giving me permission to build on my own, he invested 1 million dollars and told me to build a company. As a result, my first venture Doodad was born, and I learned that I could be an entrepreneur and a CEO.
What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?
I’ve never really enjoyed clothes shopping and wouldn’t describe myself as fashionable, but I still need to get dressed everyday and in a city like New York, you can have a lot of fun with your personal style. I’d look at Instagram and see all these great outfits but if I tried to recreate them, they’d often result in a ‘Pinterest fail’ type moment. For example, if the influencer was shorter than I, then that dress would be too short, the cute two-piece might show too much stomach or the chest area might gape. I needed to find someone the same height, size and shape as me, that liked to shop and could do the discovery to find outfits that fit us both so I could copy them. I wished I could just filter Instagram to discover these like-bodied women. But I couldn’t. It seemed totally illogical that there was no way to do this. So I started thinking about how I could and that was the foundation for creating the Mys Tyler platform.
In your opinion, were you a natural born entrepreneur or did you develop that aptitude later on? Can you explain what you mean?
I’ve always been interested in people. At college, I studied marketing and organizational behavior. I loved psychology subjects the most. This carried through into marketing, where my focus was always on understanding the user and their motivations. I think a successful entrepreneur at the core understands problems and solves them better than anyone else. If you do this, your product or solution doesn’t need to be perfect or even that good at the start. If you can really tap into an unmet need, then anything you do is better than nothing. This allows you to start small and rough, and then get traction and keep improving. I think the other component is being action-oriented, something I definitely am. I’m the furthest thing from a perfectionist, which in an early-stage startup is a blessing. So, I’m not sure anyone is a natural-born entrepreneur but I think I have always had the key ingredients — curiosity and execution.
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?
As mentioned above, my first foray into entrepreneurship started with a 1 million dollars investment from a former boss in New York. Through becoming my first investor, he helped start my journey and inspire belief in myself as an entrepreneur. He said that an idea and a person that can execute on that idea is worth 1 million dollars on their own. He was bold and backed me. He understood how quickly value can be built when you have the right ingredients.
What do you think makes your company stand out? Can you share a story?
Mys Tyler is the first social-commerce platform to serve up body-relevant fashion content. In the world of fashion, ‘fit’ has been one of the biggest problems for a while. Poor fit leads to high returns — and that’s extremely costly for the industry. Many others are trying to solve fit by helping shoppers find the right size. We know that fit is much more than a dress size — it’s about your height, shape, coloring and even just knowing how to style things. So what we do is match women who are similar, so that they can provide human recommendations — showing what fits, how it sits and how to style it. We think we are addressing fashion’s fit issue in a better way and more importantly, also creating a space where all women can feel represented. Fashion has been very intimidating historically — most models and macro-influencers are size zero. That’s normal for some women, but it’s not the general norm. This means that the online clothes shopping experience has made the majority of women feel like a minority. We believe we’re creating a better experience for all women that can not only help them find clothes that fit, but also make fashion more accessible and welcoming. We’re helping women share their style wins with their community and lift each other up.
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?
- Curiosity, or wanting to understand people, has been a character trait that’s been instrumental to my success. My first startup Doodad was a sim card that offered travelers prepaid internet when overseas. At the time roaming could land you a shocking bill so most people switched off data and relied on spotty WiFi. Competitors in this space were competing on price but what we discovered was that it wasn’t that our customers were price sensitive, they just wanted to be able to control what they were spending. Our pricing was higher, but by allowing customers to limit their daily spending, we grew a really loyal following quickly.
- Being perceptive would be another character trait. As an entrepreneur, you need to look at both quantitative and qualitative data to inform your strategy and business success — for example, you can AB test to see if people respond better to a green button or a purple button. You might find that 90% of people like green better, which makes it seems obvious that green is good…but what if 100% of people preferred an orange button that was never offered?
- Finally, I’d say being action-oriented has helped me find success as an entrepreneur. I was once told to shoot, then ready and aim. You can always improve your assumptions, but until you get started they’re all assumptions anyway and could be way off. So get some data and then work from there. There’s always more steps involved than you realize and you won’t find out until you start, so start now — it’s going to take longer than you think.
Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about the advice you’ve received that you now wish you never followed?
People have told me to “be more prepared before I do XYZ”, and I used to follow this advice…I’d wait to say yes to a speaking gig so I could get better first, or I’d hold off fundraising until I had better metrics. But you’ll always get better and thus hold off forever. The reality is you’ll get better faster by just doing it. Now I don’t worry about being prepared, I say yes or just do it. I focus my time, energy and money on doing rather than preparing. After all, in an early stage environment, these things are scarce. Have those conversations even when you’re not ready and if you feel embarrassed, then it means you’ve probably learned more than you would have with an hour of research — and head onto the next meeting. Once you have data, then you can reflect, learn and keep improving.
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?
When I worked in advertising agencies, there were always so many deadlines and urgency-driven stress. Sometimes those deadlines were real, but often it was just a culture of panic. Long hours on constant adrenaline were unsustainable for me and the team. When I moved into management, I made a conscious effort to only stress when it was really necessary. In that environment, generally, people work hard and get the job done anyway. But people really appreciate knowing what was urgent and what wasn’t, so they could better control their time and energy. That’s pretty much my motto now. I know in startups there are going to be crises that will need urgent attention, so I try and roll with the punches a bit more. Don’t stress the little stuff. And even the big stuff you have to keep in perspective. It’s not often life and death, even if it’s not ideal.
What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?
I like to be very transparent and believe by doing so it’s far easier to build trust, credibility and authority in any industry. When you are open, it shows you have nothing to hide, and often what people hide is their limited knowledge. Even when (and particularly when) you make mistakes, being honest and open about this can save you. People accept that mistakes happen and if you handle them it can be an opportunity to gain more respect and build more credibility. Back at Doodad, we were late to set up automated emails. When we did finally set up our ‘welcome’ email six weeks after launch, it accidentally went out to all customers instead of new customers only. After initial stress, we sent out a follow-up email to customers who received the email in error saying “Did you know it’s national Welcome Day, that’s why you’ve received an email when it might have seemed a bit late”. Customers thought it was funny and it ended up building our persona with them.
I also like to educate and share knowledge. Some entrepreneurs are careful with what they share as they don’t want others to steal their ideas. I don’t worry about that too much as I know it’s how you respond to what comes up tomorrow that’s going to make the difference to your success, not what you know and what you’ve done today.
Can you help articulate why doing that is essential today?
We have so many options everywhere we look, which makes it really hard to cut through the noise. When you do manage to do this, you want to make it easy for people to choose you. If you’ve developed credibility, this becomes a lot easier. Once you have customers, you then need to keep them. When things go wrong, having a relationship with your users will make them more tolerant, and my advice is to over-communicate in these situations — if they know you’re working on issues and trying to improve, people will be more forgiving and patient.
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?
The most common mistakes would be overinvesting before they’ve validated their ideas, spending too much time planning without executing and assuming things will be faster and cheaper than they are.
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”?
If you’re building a startup and want to attract angel or VC financing, then you need to think about the statistics. Startups are very high risk — something like 95% of businesses fails, but if they succeed they could be the next tech unicorn. Early-stage investors know the risk and do it for the potential unicorn. They’ll invest in a portfolio of companies hoping that one is a big winner. When choosing who to invest in, they want to see you have a path to being a billion-dollar company (quick rule of thumb: show you can get to 100 Million dollars ARR in five years). So essentially, the outcomes are pretty extreme — you’re either working on a company that could be a bust or a billion dollars. As an entrepreneur, you’re likely working long hours, you often won’t have a salary at the start, and even when you do it’s minimum wage and substantially lower than you earned in the past, so you’re not only investing your time and energy but financially too. Add that together, and you’ve got a highly stressful, risky and personal venture. At the beginning, you’re also figuring things out. There’s no blueprint for a startup, which means you’re going to be making mistakes, wasting money and you’re running on a limited ‘runway’ (the number of months before you run out of money). When things go well — you get investment, a PR win or great customer feedback — you think you might just pull it off. And then a moment, day or week later you have a setback and can feel like it’s falling apart, such as an unexpected cost, investor drop out, bug in your build, or public criticism. This rollercoaster is all part of the journey and no matter how bad things seem, keep going because you never know what’s around the corner.
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.
Before Mys Tyler’s launch, we reached out to many stylish women who we wanted to bring on as contributors to our platform. Some understood our vision, and others didn’t respond. Immediately after launching, however, we heard back from various women in the end who said “sorry we didn’t totally get it at first…is it too late to join you?”. During Mys Tyler’s launch week, we found that many of the women we were outreaching to had already or were in the process of signing up! So this was an unusual high, as progress is often so continuous that it’s hard to spot the changing of the tide. In this instance, it was incredible to see so many influential women signing on and see the current move Mys Tyler forward.
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.
The nature of pitching to investors means getting rejected by investors. Even though you know this is inevitable, it still hurts. Some investors are great at letting you down gently — keeping the door open to future partnerships — while others are less delicate. I’ve had feedback directly and sometimes indirectly, which is worse — where people have said I was naive and didn’t know what it takes to build a marketplace or run marketing. Having people doubt your ability or underestimate your experience and drive is tough. It’s natural to have your own doubts, so these can be triggering and make you feel vulnerable at times throughout the journey.
Based on your experience can you tell us what you did to bounce back?
Remember that it is a rollercoaster and you don’t know what tomorrow will bring. You get used to the swinging pendulum, and when you’re down you just think “I must be ready for a swing now”. Another thing I do is look back at some of the positive feedback we’ve had from our customers and contributors — seeing that we’ve already had a real impact on people is a great way to have a sanity check and remember that we are doing something important. One of our contributors posted to Instagram that it was so important for her to be a Contributor with Mys Tyler because she’d struggled with body image before, and now wanted to reverse that narrative. Another customer replied to an email that at the age of 78, she finally felt human and content, after feeling less than her whole life. Far too many women struggle with body image and it can be crippling. To know that we’re helping some women feel more supported and represented, as well as establishing the narrative that all sizes are normal beyond size zero, makes me feel so great.
Ok super. Here is the main part 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.
- Document your wins and your misses. We’ve started tracking our ‘wins’ and ‘misses’. on a quarterly basis to help reflect how far we’ve come as they are easy to lose sight of, both in terms of what we thought was exciting then compared to now, and how many issues we’ve been able to overcome. It’s a great reminder that you’ve got this and can keep navigating through whatever comes next.
- Take the time to imagine the future. Having a clear vision helps you ride the bumps without getting deterred or distracted. We do an exercise as a team where we imagine what we’ll look like in 5 years — how many staff we’ll have if we’ll have global offices, what people say about us, what impact we’ll have on the world. The more color you give this, the stronger it holds.
- Balance. Try to have balance but also allow yourself to ditch that concept temporarily. People say it’s a marathon, not a sprint, but when you’re in a startup it feels like both. To keep yourself mentally, physically and emotionally able to run the race — focus on eating well, exercising, making time for friends and family and having downtime. That said, sometimes you’re in a crunch and you let that stuff go. Sometimes you’ll be so exhausted that you should give yourself permission to ditch the gym, and be anti-social for a while to just rest your body! We can’t do it all. But longer-term, the more balance you can keep, the better.
- Find your cheerleaders. Having supportive people who understand what you’re going through can be all you need on a tough day. I have one friend Courtney that sends me motivational quotes on a nearly daily basis — sometimes they are so corny they make me laugh — but it’s this constant positive energy that really feeds me. Conversely, be really careful with the investors you bring on, make sure that they are supportive of you as a person. Startups are hard, you put all your time, energy and money into them. You don’t want investors to make your life harder, they should say “how can we help”. In the early days, it may feel like you can’t pick and choose — but you can and you should!
- It’s ok to say no. When you start you want to say YES to everything and I’m a big believer in this…sometimes it’s the conversations or meetings that you thought were insignificant that turn into the biggest opportunities. But at the same time, even the biggest opportunity is not worth your sanity. Only you know what you can handle, and sometimes no is the right answer.
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?
I think a big part of resilience is showing up. Things go badly — and you need to just show up again. You may get embarrassed because you didn’t prepare for something or you jumped in the deep end. Keep showing up, because you learn through every experience and it makes you better today. Knowing that there will be many setbacks and moments along the way that makes you uncomfortable helps — as while it never feels great, you just have to keep going.
Did you have any experiences growing up that have contributed to building your resiliency? Would you mind sharing a story?
Growing up, our family went through periods where money was really scarce, so I started working early and didn’t perceive that I had the luxury of a safety net. So I couldn’t just quit my job if I didn’t like it or be too choosy. When things aren’t an option, you just make the most of it and continue on.
In addition, many of the companies I’ve worked for have been challenger brands, which often have fewer resources, support and brand awareness. This teaches you to punch above your weight to compete and put yourself out there, even though you may feel less prepared and of a specialist than others around you. I think this helped with building my resiliency.
In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?
When things are difficult, I think about the worst possible scenario logically and how I’d handle it. Once I’ve done that, I know there’s a path through it. That takes the pressure off and helps me get out of crisis mode, so I can focus on getting a better outcome.
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.
Saying yes and being open builds a culture of innovation. It’s really easy to find reasons to say no to various opportunities — whether it’s because you don’t have time, it’s a distraction or not what you do. While these can be great reasons to say no, this often gives you permission to not consider the opportunity or idea fully and throw it out too easily. A former boss at Mint Mobile would challenge our leadership team to consider opportunities as if we had said yes. This exercise would help us envision what we’d need to do next, how we’d rearrange resources and make it work. In the end, once we knew we could do it, we might still decide not to proceed. But this more positive, open outlook allowed us to realize opportunities bigger than we had imagined in the past. Taking these leaps fueled our imagination and the company’s hyper-growth.
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?
My friend Courtney Howell had this quote on her desk when she was building her first company: “The harder I work, the luckier I get”. I really love this one. So much of it is luck, but if you do the work and put yourself out there, then you’re also creating opportunities.
How can our readers further follow you online?
We have been documenting what’s happening in the world of Mys Tyler since we launched the company on Instagram and the app. In addition to our regular content, we also have a dedicated Startup Series section covering marketing, staffing, branding, fundraising and more, which we update weekly on Instagram and the ‘forum’ tab of our app.
This was very inspiring. Thank you so much for the time you spent with this. We wish you continued success and good health!