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Celebrating Love in All Its Forms: the Co-founding Stories of Three Startups Founded by Two Best Buddies, a Couple, and a Sibling Pair

Tuesday Feb 14,2023 | IIE News

Celebrating Love in All Its Forms

Valentine's Day is a time to celebrate love, and what better way to do so than to highlight some of the inspiring BIG startups founded by those who share a special bond? Whether it's siblings, couples, or friends, the dynamic duo behind these startups is proof that love, kinship, friendship, and entrepreneurship can go hand in hand.

In this feature, we'll be introducing you to three startups that are working to create a big impact in their respective industries and inspiring others to pursue their passions. We'll also share their journey as co-founders and tips for anyone interested in co-founding a startup. Discover their stories as we celebrate love, entrepreneurship, and the power of teamwork on this special day.

Share with us more about your startup, including how you all met and what inspired you to join forces and embark on this entrepreneurial journey together.

Roshan & Charlie

Roshan & Charlie: We’re Roshan and Charlie from Vita, we make software for mid-sized enterprises to reactivate their past applicants for current hiring.

So, back in our poly days, Charlie had long hair as though he were in a rock band, and on the very first day of school lunch, this boy pulled out a whole baguette from his backpack. My mind just goes, “I've got to talk with this guy.” We bonded over our common interest in building stuff and solving any problem we can find. We built our own smart home sensors, made an app for our clique called ‘Squad’ that shared live location, memes, a lame-joke counter (there were too many of these), and also bill splitting long before any of these apps were a thing. Then we went on to take part in almost any kind of competition we saw, which funded many of our projects. Something about the joy of seeing what you came up with being deployed on a massive scale was appealing to us. When we came across our current problem statement, the possibility of helping millions of people find better employment, it was a no-brainer.

Maryann & Bryan

Maryann: I'm Maryann, Co-Founder of Lexly Health and my Co-Founder is Bryan. Lexly Health is a preventive health-tech startup that focuses on reducing the risk of chronic conditions. Instant feedback is given to correct their exercise posture using AI (Computer Vision).

We are siblings! Bryan is my elder brother. Bryan was working in a tech role and experienced back pain as well as numbing fingers himself. At 24 years old, he was told that he had the body of a 40-year-old. That scared him, especially since he thought that he was young and healthy. Back then, I was also experiencing lower back pain. I resonated with him when he told me what he was experiencing and the both of us decided to work on Lexly together to solve our personal problems.

Sherritze & Jeremy

Jeremy & Sherritze: We are 2 fresh graduates from SMU who came together to work on Aerealm when we were both in Year 1. From our love of digital marketing and entrepreneurship, Aerealm was then born. Aerealm currently functions as a lead generation agency that pools together resources from individuals to create communities that allow us to launch larger and more effective campaigns for them.

We met through SMU like many university couples. As we both were not fans of the corporate world, unlike many of our peers, we already knew that we wanted to work on something of our own. Due to my interest in digital marketing and his interest in automation, the idea of Aerealm simply made sense. We ended up venturing specifically into the Financial Services industry simply due to the network we established there from the start.


Were there times when you both considered ending your partnership? How did you work through those difficulties and maintain a successful collaboration?

Roshan & Charlie: We’ve had our fair share of tiffs – mostly when fatigue sets in. There are times when we had to work through 48, 60-hour sprints. At that point, anyone breathing nearby would annoy us, let alone have different views on several large-scale questions. We quickly realised - when this is the case, taking time to rest up is critical for success. Then of course, whenever any of us feels something isn't right, it is important for us to communicate our feelings transparently and address our perspectives in a post-action review, a safe space to confide in whatever external and internal factors are affecting us, this is key in building the working relationship and understanding between the founders.

Maryann: I don't think so. But we faced challenges at the start where we had to figure out how to work with each other because of our different working styles. We overcome it by having open communication through daily standups in the morning. If we experienced any challenges, we would talk about them from our own perspectives on why we acted or felt a certain way. Something that I really like about our standups is that we check in with each other on our work mood and personal mood on a scale of 1-10, and give each other the space to describe how we are feeling.

Jeremy & Sherritze: Definitely. Being a couple and business partners often meant disagreements that could seep into our relationship at times. We overcame this by establishing clear roles so that there would be one final decision-maker who could end any stalemates. If it had to do with the marketing aspects of the business, I would have the final say. Whenever it came to the strategic direction of the business, he would have the final say. We found that having this system allowed us to move on from conflicts easier as one person would be given carte blanche.


What was your favourite part of working together?

Roshan & Charlie: We've been the closest friends since poly, so we have a very nice dynamic; aside from that, we have very complementary skill sets; Charlie builds the product, and I ship it. If we didn’t think the other was the best at what they did, we wouldn’t be in this. The ability to trust and rely entirely on someone, is probably the most ambiguous kind of job you’ll find anywhere - knowing that your partner has the same shared amount of dedication and will put in their best effort is one of the most valuable things.

Maryann: Celebrating small wins and milestones together! Whenever we made good progress after a client's meeting, we would treat ourselves to a good meal or dessert after. Both of us have a sweet tooth so desserts always do the trick! It also brought both of us closer together because it was easier for both of us to talk about anything.

Jeremy & Sherritze: The best part of working with your partner is that we could easily understand each other quickly. While disagreements were part and parcel of the job, it also meant that we were essentially trained to tackle multiple conflicts regularly. Of course, having someone who is working on the same vision as you made a lot of late nights and missing important events a lot simpler too!

Thank you for sharing your experiences. As seasoned co-founders, what questions do you recommend potential co-founders ask each other before embarking on a startup journey together?

Roshan & Charlie: We’ve seen and personally heard too many stories of founders falling out along the journey. Based on my experience, I think two main key factors stand out:

  1. It is important to establish the founders' shared vision of what the company will grow into, and how their personal careers figure into this.
  2. Secondly, is the working dynamic. We all have our favourite teammates for our projects because some personalities just work better together.

Charlie and I have worked on numerous projects, in fact, many serial entrepreneurs carry forward the same founding team members, and that is why it is so common that startup co-founders were ex-colleagues at some point.

Maryann: Some key ones are finding out whether your Co-founder has the passion to work on the problem you are trying to solve, their personal motivation, and their way to deal with bad situations. Startups are an intense and taxing journey so it is great to have someone you can trust during the tough times.

Jeremy & Sherritze: What is their 10 years vision for the company? It is always important to establish a long-term goal to ensure you're both on the same mission!

Any last words of advice for solo entrepreneurs looking for a co-founder?

Roshan & Charlie: A co-founder is a long-term partner and relationship. Innovating an idea that is very new can also be a lonely journey where you will have to second guess everything and if you’re not doing that, you’re likely not looking at it from every angle, and that just means sub-par decision-making. Find someone you respect, enjoy spending time with, and have a similar commitment to the cause with, those are the key factors that drive things forward for us.

Maryann: Many startups die of suicide and not murder, and one of the reasons is when founders fall out due to misalignment. Find your Co-Founder like you're finding a spouse/partner. Find out what makes them tick and someone you can potentially work with for the next 3-5 years.

Jeremy & Sherritze: Having a co-founder can prevent narrow-minded decision-making by providing a different perspective. We recommend finding somebody who is able to challenge you. While it can be frustrating at times when differing opinions arise, we'd argue that these differing opinions are what challenge us to think differently and further before making strategic decisions.

Discover their innovative solutions at the following links: Lexly, Vita Verify, and Aerealm.

These startups were part of the Business Innovations Generator (BIG) programme, a 4-month equity-free incubation programme aimed at fostering the success of early-stage startups.


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