In this candid conversation, JJ reflects on his remarkable journey, from gaining admission to Stanford GSB to founding Onloop. He discusses his proudest achievements, the challenges of building a pioneering company, and the invaluable lessons learned along the way. JJ also shares his vision for Onloop in the evolving landscape of remote work and generative AI, his approach to angel investing, and offers insightful advice for aspiring entrepreneurs. Join us as we delve into the experiences and insights of a trailblazing entrepreneur committed to transforming the future of work.

HanYue: You have accomplished a lot in your career. What’s your proudest achievement so far?

JJ: My proudest achievement remains getting into the Stanford GSB MBA program. Before Stanford, I had spent my entire life in Asia. Moving to Stanford marked a significant shift in both my career and personal development. Immersing myself in the challenging yet enriching environment of the Bay Area was transformative, and I just returned there for my 10-year reunion.

HanYue: Can you tell us about the origins of Onloop?

JJ: Onloop originated from personal frustrations I encountered while managing teams at Uber for 3.5 years, especially with inefficient HR processes. This led to extreme frustration with the outdated systems. After leaving Uber in September 2019, I started OnLoop to solve some of these frustrations. We developed our first product around changing how performance reviews get done using GPT3 in early 2021. We’ve come a long way building out our platform and focused on helping every manager become a great manager using habit-forming technology and applied AI It’s been an exhilarating journey, shaping a company that contributes to the evolving future of work landscape especially given all the transformative impact of distributed & hybrid work as well as the maturity of large language models (LLMs).

HanYue: What have you learned from building Onloop?

JJ: Building Onloop has taught me that a founder’s longevity hinges on their conviction in their mission and the people they surround themselves with. Pioneering in any field is incredibly challenging—far more so than creating a copycat startup. Jensen Huang famously said he’d say ‘hell no’ if asked to do it all over again. The world resists change, and you must consistently challenge the status quo. 

Growing up in an Asian household where academic success was prioritized and entrepreneurship was uncommon, taking a non-salary path wasn’t easy. This background often amplifies the voices of doubt during challenging times, yet confidence and eloquence are the most significant drivers of success in the early days. 

Life in your late 30s and 40s has many more responsibilities with respect to family so it’s not always easy to take the plunge, but the learning experience from entrepreneurship is absolutely invaluable. I’m better off for it, even if things don’t pan out as expected. Starting a company is like becoming a parent—it’s a transformative experience that teaches you new ways to live.

HanYue: What’s your vision for Onloop?

JJ: Our vision at Onloop is to help knowledge workers fully realize their potential during this era of significant transformation. The rise of remote work and the advent of generative AI—akin to an industrial revolution for knowledge workers—presents new challenges and opportunities. We aim to help these professionals optimize their careers in a rapidly changing environment. The knowledge work sector is vast and often influenced by chance, especially in job placement – knowledge worker wages are a multi-trillion dollar asset class allocated by chance. My goal is to develop and disseminate optimal strategies for knowledge workers, enabling them to seize the best opportunities available.

HanYue: Tell me about your angel investing career and how it impacts your entrepreneurship journey.

JJ: I don’t subscribe to the notion of work-life balance but prefer to maintain a purpose portfolio, which currently includes my family, OnLoop, and enhancing Singapore’s status as a global hub, especially for highly innovative companies. My approach to angel investing focuses more on the people than the ideas themselves, reinforcing my belief that the right people drive success. And I apply this same principle in my work with other CEOs and founders.

While I believe any manager can become great with the right support, a CEO doesn’t have a direct manager, making coaching essential. I therefore coach a handful of founder CEOs and  this interaction offers mutual learning opportunities and enhances my own growth as a CEO/founder 

Talking about angel investing, it isn’t just for the rich and wealthy. I have made six investments so far in the range of US$1,000 through syndicates to US$15,000 in certain founders that I know personally. I have learned that while my bets on ideas have failed, my bets on people have not. This supports my hypothesis that early-stage investing is 80% about the founding team. 

Lastly, having become a Singaporean last year, I feel even more committed to the Singaporean ecosystem and proud to build in it.

HanYue: Advice for young entrepreneurs these days? 

JJ: When I was single and enjoyed partying, I never imagined I’d find myself here today. People seek pleasure when they lack purpose, as Victor Frankl famously spoke about. Today, living a life of purpose is crucial for happiness — it involves engaging in activities that you deeply enjoy and believe are your calling. This philosophy has guided both my personal and professional life and serves as my constant motivation. 

JJ’s journey exemplifies the blend of purpose and innovation needed to navigate the evolving landscape of modern work. His insights into entrepreneurship, the importance of mission-driven leadership, and the power of transformative technology offer invaluable guidance for the next generation of innovators.

If you’ve ever ordered boba, you’ve probably used Snackpass before. Snackpass is a fast-growing startup that operates a social food-ordering app alongside a suite of software and hardware solutions for restaurant operations.

Boasting a $400 million valuation, Snackpass is backed by a slew of the best investors around, including Craft Ventures, a16z, General Catalyst, First Round, and Y Combinator. I had the pleasure to sit down with Snackpass’s co-founder and CEO, Kevin Tan, to talk about his background and experiences.

JOURNEY TO BECOMING A FOUNDER

My first question was if Kevin did anything entrepreneurial before Snackpass:

I had multiple projects before SnackPass. As a kid, I shot a movie with friends and made a comic book to sell. In college, I picked up programming, which sparked my interest in technology startups. I started that in my sophomore year. I tried a few different projects or companies and started SnackPass in my senior year.

Back in college, Kevin actually majored in Physics, not Computer Science. I asked Kevin what made him decide to pursue software over a career in Physics, and also why he decided to start a company as opposed to joining a big tech company:

I actually initially started in the humanities. After a year of humanities, I went and moved into Physics and started programming at the same time. I chose software because I felt that things were a bit more fast-paced in the world of technology. Also, I didn’t feel that I was going to be a top 1% physicist–though I still really enjoy Physics. As far as pursuing a startup instead of big tech, I did actually apply to Google for an internship, but I didn’t get in. One of my favorite things about startups is that you don’t necessarily need to impress any gatekeepers who hold power over your next job, you can go make your own! That’s something that made me super excited about startups.

STORIES AND THOUGHTS ABOUT SNACKPASS

I remember sometimes to get to the restaurant owners, I would set up a meeting and then trek across campus in the cold and in two feet of snow only for the owner to say “Oh, I rescheduled”, yet I always followed up and went back to meet them.

Kevin Tan

In an article by Free Ventures about Snackpass, I read “In the beginning, they partnered with restaurants by going door to door to mom-and-pop shops and talking personally with the owners. They also posted a bunch of flyers around campus and created referral mechanisms on the app to get the word out.” I asked Kevin what that experience was like:

Back then, we didn’t have any funding. We got rejected from Yale’s incubator, let alone venture capital. But we were able to get pretty far because I was able to code and go door to door to bootstrap our first set of customers. I’ve always had a very determined attitude about things and am willing to brute force it if I have to. I remember sometimes to get to the restaurant owners, I would set up a meeting and then trek across campus in the cold and in two feet of snow only for the owner to say “Oh, I rescheduled”, yet I always followed up and went back to meet them. Obviously, there needs to be a more efficient way to do that, but if you’re trying to learn something very quickly. That’s one way to do it. 

Even to this day, we’ll go to new installs and try to embody the customer as much as possible. It’s very hectic behind the restaurant counter. To make a product like ours work, we have to get very deep into how the staff interacts with our tech and how they are receiving orders. Like, were the printers printing? Were they able to confirm the order or did it get missed? 

As Kevin hinted in his answer, Snackpass started at Yale, then expanded to other colleges, and is now expanding to all restaurants. I asked Kevin how he decided it was time to expand to new markets:

There’s this blog post from Marc Andreessen about how there are two phases of a startup. One is before product-market fit, where you should do everything to find it. The second is after product-market fit, where you should do everything you can to exploit it. I think you don’t want to scale anything up before you have really strong product-market fit and a repeatable engine for driving revenue or growth. You can have an amazing product, but if you can’t get it out efficiently, that’s going to be a problem. 

Whenever I think about the restaurant business, one of the first things that comes to mind is the pandemic. I asked Kevin how the pandemic affected Snackpass:

It was definitely a huge curveball. At the height of the pandemic, people were asking if college campus restaurants would stay in business. People went back home. We saw a big dip in our volume in the same way a lot of local marketplaces did. We used that time to ask how we were going to expand outside of college campuses. The pandemic motivated us to shift our whole business model. We shifted into focusing on building an operating system for these restaurants, and we’re still playing that out today. 

I asked Kevin how Snackpass’s go-to-market motion has evolved over the company’s lifetime:

In terms of target customers, we’ve grown from just SMB restaurants to having some multi-location mid-market brands using us. In terms of how we acquire new customers, we get some inbound by being a market leader. Having a brand name and social proof is very important. Other channels that have worked for us are referrals and social media such as Instagram and Tiktok.

In a previous conversation I had with Gusto’s cofounder, Eddie Kim, he talked about the idea of sometimes needing to turn down larger customers and contracts to remain focused on the target customer. I asked Kevin if he ever thought about this:

Yes, we’ve definitely had to turn down some large potential customers. As a rule of thumb, larger and more enterprise-y customers tend to have more requirements, move slower, and want integrations and things that are not standardizable. These are often one-offs so we don’t get as much leverage with what we’re building. 

Unless your strategy is enterprise-focused, you probably want to focus your angle of attack on one segment. There’s a good book called Crossing the Chasm. One point it makes is that the market you go after should be a single entity, one with a common set of characteristics and needs that you can address as a whole. We’ve definitely had to find our niche because there were customers asking all sorts of things. In the world of restaurants, especially, there are so many different varieties operation-wise, that you can get pulled in many different directions. Sometimes it’s tempting to chase revenue, but that can easily lead to a very overreaching product surface area. It’s better to have a narrower angle of attack, generally speaking.

A key differentiator of Snackpass compared to other food-ordering apps is the social components of the app. In Snackpass, you are able to gift points to a friend with each order you make. Once you accumulate enough points from someone, you hatch a mini digital chicken–sort of like a minigame. I asked Kevin for some cool or surprising ways he has seen people using these features:

Oh, there are tons. There’s a feed where you can see who’s sending gifts to whom. The idea behind the feature was to give users a social way to figure out what restaurants are interesting or popular, but we’ve heard some people use it to see who’s flirting with whom. It’s kind of a sneaky way to get a closer look at some people’s relationships. Another cool one is that we’ve heard many anecdotes of someone sending points to all their co-workers in an office and then they not only try out Snackpass but also try out the restaurant the person ordered it from. It’s a win-win.

BUILDING A TEAM

I’ve talked to many founders and culture is brought up time and time again as something that is extremely hard but important to get right. To kick things off, I asked Kevin how to fire people in a way that minimizes the negative effect on the wider team:

I believe this is something that I, and probably many others, can always improve upon. I strive to excel in this area, though I’m not sure if I’ve reached that point yet. Having clear expectations, like a Performance Improvement Plan (PIP) process, is crucial. This way, it’s not a surprise when someone is let go. If we fire someone,  even though they may not realize it yet, they’re better off being successful somewhere else than being unsuccessful here.  It’s painful at the moment to be rejected or to reject someone, but it’s a necessary step to ensure both sides are in a situation where they can thrive.

I also asked Kevin what Snackpass’s cultural tenets are, and what he does to implement those tenets in practice:

Our slogan is that we are humble and hungry. On the humble side, part of it is being easy to work with, which facilitates collaboration. It’s also about asking questions, acknowledging fallibility, and striving to prove yourself wrong. It’s about starting from a position where you just want to learn and get closer to the truth. Having an ego can blind you to the truth, I’m also guilty of this. Sometimes pride prevents you from admitting you’re wrong, even subconsciously. You have to put that aside to find the right answer. That’s the humility side. The hungry part, obviously, we’re a food company, but we also look for people who have a chip on their shoulder and are willing to work hard. There’s nothing more demotivating than having part of your team that’s really hard-working and driving towards success, and then having others who are indifferent about it. So we generally want a team that is really hungry, ambitious, and genuinely cares about the outcome.

Some founders say they want to be completely authentic with their team, sharing their concerns or fears. Others want to always project confidence to avoid worrying the team. I asked Kevin how he prefers to show up:

I tend to wear my emotions on my sleeve and I’m quite transparent. If I’m excited or annoyed about something, I’ll show it. My co-founder, on the other hand, is better at separating her outward expressions from her inner feelings. It’s just a stylistic thing. I’m quite transparent. My co-founder and I balance each other out in many ways, including our aptitudes, styles, and communication methods.

Being a founder comes with a lot of very low lows, so I asked Kevin how he copes with the lows:

I realized that being unhealthy doesn’t make you better at your job. So, I started going to the gym and running. I see time away from the computer as just as valuable. Sometimes, you might be working hard in the wrong direction. It’s better to pause and think for a moment. The concept of working smarter, not harder, is crucial in technology and startups. You can spend years going down the wrong path. It’s important to always be asking questions and self-correcting your direction. This doesn’t always require hours of grinding. Sometimes, it just takes a clear head. 

I asked Kevin if his reflection time always took the form of exercise, or if it was anything away from work:

It could be taking walks or reading. There are some really good books that provide frameworks that expand the problem space even further or help me view problems from a different perspective. I like to read a lot. I also like to exercise and play music. It’s just something that isn’t focusing on the immediate problems in front of me. Sometimes, you can think really hard about something, but once you talk it through with someone or test it, you get so much more information quickly. You get out of the narrow set of parameters you’re working with.

ASIAN AMERICAN TALK

Anecdotally, I’ve noticed that a lot of places that use Snackpass are Asian restaurants. I asked Kevin if this lined up with reality, or if it was all in my head:

No, it’s not just you. We’re at a lot of Boba shops, for example. Part of it is because we initially launched on college campuses and there’s a lot of Boba near colleges, especially at Berkeley. I think it’s one of the most dense Boba areas in the country. We started off with just mobile order and pickup, and that has evolved into self-serve kiosks and digitizing the experience without a human in the loop. This has been particularly popular with Asians, especially Boba shops. It’s an interesting question as to why. I think we’ve found that Asian owners and operators are very practical. They see that it saves them money and increases efficiency, so they adopt it.

Next, I asked Kevin to tell me about his Asian background, and how it has impacted his own life journey, especially as a founder:

I was brought up by Chinese parents. They came from China for grad school. My dad arrived with only $50 in his pocket. My mom worked a full-time job while also taking care of me. I also spent a lot of time with my grandparents since my parents were working full-time, so they were also hugely influential for me.

I grew up in Ohio, where there weren’t a lot of Asians, so I grew up with a deep-seated feeling of being different and being an outsider. As a child or a teenager, I wished to fit in more with the mainstream. At some point, I learned to embrace going against the mainstream and being different. To this day, all my heroes are people who are counterculture and really go against the grain. As a founder, having a strong STEM background is helpful and I thank my family for that. My grandfather taught me math several years ahead of what I learned in school. It’s cool to see Asian-American founders like Jensen Huang or Tony Xu rising to the top. If you look at top leadership, a huge amount of them are Asian American, so I’d say that there’s a good match between tech and our culture. But, there’s also a sense of a bamboo ceiling. It takes time to break through that. The more examples there are of successful Asian leaders, the less of a bias there will be.

You know, the recent popularity of Asian culture has been incredible. Take K-pop for example, it’s like the new Hollywood in Korea. I feel like the 20th century was a century of unspeakable suffering for a ton of Asian countries. Our parents, my dad grew up in the cultural revolution and his dad went through the worst century of humiliation. Now, in the 21st century, I feel like they suffered for us to really thrive. Maybe this is the century where you see Asians globally–not just producing semiconductors or T-shirts–but being the cultural center of the world. 

SHOUTOUTS

Leaning into the cultural aspect, Kevin wanted to shout out a few of his favorite Asian American artists, namely EDM artist ZHU and the 88rising crew, especially Joji, please go check them out!

Also, if you ever find yourself looking to order food, consider using Snackpass! They often have great discounts and you can earn loyalty points which can be used to redeem free items. You can download Snackpass on any of the major app stores.

 If you own a quick-serve restaurant, please check out Snackpass’s offerings at https://www.snackpass.co/. Snackpass’s platform is trusted by many mom-and-pop shops as well as brands such as Sharetea, Somi Somi, and Pokeworks.

Thank you for coming to the newsletter, Kevin!