Convergence Conversation: Service Leadership Innovation with Diana Tsai

It was 2015 when Diana Tsai introduced herself to me. She was the co-founder of a startup called Veterati, which was launching to help connect military veterans to mentors to help them transition to the civilian workforce. Seeing my background on LinkedIn, she reached out to ask whether I would be interested in beta testing the new capability. That first conversation bloomed into a relationship that has lasted for years and has given me the chance to give support to the beta testing but also to become one of the company’s first mentors.

Diana is a serial entrepreneur driven by self-discovery, self-awareness, and a passion to solve humanity’s pain and suffering. A Forbes 30 under 30 Social Entrepreneur, Diana has an incredible runway for making a continued positive impact on global communities as well as the people in her life through service leadership innovation. She is an authentic leader who consistently states her belief that the companies shaping the future of humanity are built from the inside out which starts with knowing ourselves.

In this Convergence Conversation, Diana and I discuss how people and businesses are evolving to serve higher purposes. We explore the potential of technology to connect people in a deeper and more meaningful way, and what it means to lead from a place of service to others.


Innovation Rooted in Service Leadership

Deb: All of the companies you have started seemed to have the theme of human connection. Where did this passion come from?

Diana: I’ve been drawn to service my whole life. When I think about connection, I think about a Confucius quote I’ve been contemplating for about a decade. In effect, he said that to be able to serve the nation or to be able to serve the world, you need to be able to serve your community. To be able to serve your community, you need to be able to serve your family and your friends. To be able to serve your family and friends, you must be able to serve yourself and know your heart is true. There’s a bit of paraphrasing here, but to me, it defines what a connection means. A connection functions on all those different levels — the connection to self, to your friends and family, to your community, and your nation. There is also a connection to humanity. All of those connections are worth investing in. And at different phases of my life, I have invested in them by building companies around the different types of connections in different arenas.

Deb: Where do you think this manifests from?

Diana: From a very early age, I started thinking deeply about the question of what constitutes a life worth living. I remember being a teenager and thinking, what is this all about? What’s the purpose of life? Eventually, I settled on service. There’s really no life worth living if it’s not in service of others. In particular, it was the question of why I should invest so much energy into growth and learning if not to serve. Because it sounded pretty selfish. We have these pursuits from a young age, to learn things, go to college, and become successful. The question is why does it all matter? It seemed like none of it mattered unless it was in service of someone else.

When I was younger, I read voraciously. There was a specific period where I was obsessed with reading everything I could about the world wars and the Holocaust, mostly to understand how people could do such terrible things to each other. I remember a lot of writers saying, we’ll never let this happen again. 

As a teenager, I learned about Darfur. It was devastating to me. I stayed up for an entire night thinking about what was going on and by morning had decided there were two things to do. One would be a longer-term effort, realizing that these tragedies happen because of systemic issues and many because of political issues as well. So I decided I would go into politics. The second thing was recognizing that people were dying and suffering right now, so we had to do something now. I started getting involved with nonprofits and working to galvanize community action.

Social impact problem solving around major social issues was the first thing that I was drawn to, not entrepreneurialism. Startups became a vehicle for doing social good in my career. Human connection is a big theme because so many of my most meaningful experiences in life came from human connection. It’s a framework of what kinds of connections matter and how to facilitate to cultivate and nourish intentionally different levels of connections.

Building Human Connection

Deb: You use technology to make those connections in your business, but you talk about the brand as human-centered. How is human connection changing with technology?

Diana: I really love that you recognize the fact that many of the companies and brands that I work on center on human connection. I do it because I fundamentally believe that human beings are the solution. Whenever I see a problem, the solution is other human beings. That’s why the connection is always the solution. If veterans are struggling with employment, the solution is human, because 80% of jobs come from our personal networks. Therefore, there is no other possibility besides connecting veterans to mentors. It’s why I started Veterati. The same is true with my company twine. If loneliness affects 50% of Americans, the solution is other people. There are 350 million other human beings to connect to. Let’s connect people to each other. There’s this element of people who are the solution to people’s problems. It makes sense.

People have become more transactional and the transactional nature of our connections has to do with volume. Before, there may be only 30 humans in your village or tribe. They may be the only other people you would meet in your entire lifetime. But now, you can meet literally millions of people. That shift can desensitize us to the quantity of connections that are possible or we can see the incredible opportunity — you could meet a million people in a lifetime. Deciding which one it is depends on  the intention with which we approach relationships.

If you have the intention of nourishing and discovering deep, meaningful connections with a million people, then all of a sudden there is richness in your social networks. Your social capital dramatically increases.

A friend recently reminded me that our technology has become highly evolved, but unfortunately human beings aren’t so highly evolved. When you put highly evolved technology in the hands of unevolved humans, it can create scary situations. The key is to evolve humanity. If you have highly evolved technology combined with evolved humans, then you get all sorts of beautiful things. The questions to ask are: how might we evolve our relationship with ourselves and others? How might we create connections that flourish and add deep value into each other’s lives?

Purposeful Human Networks

Deb: Do you think we focus on the transactional aspects of connection because they support our internal needs so we can get to the larger purpose at some point? How does it work for businesses?

Diana: I’m obsessed with the concept of Deep Networking, a phrase I came up with in 2020 when I published a piece on the concept. The way I think about networking sort of operates on Maslow’s hierarchy. Transactional networking is our most basic need. It’s operating at the same level and function as the need for food and shelter. It’s nothing more than “I have a product that I want to sell to you, please buy it.” As business evolves and business professionals evolve, they go up Maslow’s business hierarchy, and also unlock new customer markets with equally evolved customers. This is why a lot of brands are super focused right now on social impact to reach millennial consumers, 83% of whom want to work for and buy from brands that align with their values. It is at this point where you start to think about the opportunity to heal or to alleviate suffering, or to bring more joy to people’s lives. It’s about having a mission and asking others to join in. This is a different way to approach business.

I’m conscious of the fact that companies have to go up Maslow’s hierarchy at their own speed. When you’re in start-up mode, you are just trying to survive. But when a company is performing soundly and at the top of their game, or specifically looking to resonate with customers and clients that are more evolved and less transactional, that requires moving beyond transactions.

I feel lucky to have understood this reality early in my career. Beautiful things happen when you have non-transactional relationships. All my best business relationships have come out of deep relationships. I don’t have business relationships. I have friends I work with or want to work with someday. 

I’m working right now on four different startups with four different teams. These teams came from completely non-transactional relationships that were all friends. So often, I meet someone and think this person is so talented, I just want to watch them grow or help them with their journey in any way I can. Then lo and behold, years later we’re working in a company together. This happens repeatedly. I’ve learned to trust it. This thought process has unlocked unusual things and rich experiences that are so important and meaningful to me. To be able to work with people I love, care about, and respect is incredible. I don’t want to operate on any other level.

Something Truly New

Deb: Do you think your business experience is unique or is it common across business?

Diana: That’s hard to answer. From a data perspective, I don’t know. But I wrote a LinkedIn article on Deep Networking asking questions such as what if networking went beyond transactional? What if networking was about getting to know each other as human beings? What if networking was around understanding motivations, deep listening, and understanding everything about you as a human? 

The response was intense. If I tried to publish something like this five or six years ago, I think the response would have been much less accepting of the concept.

There seems to be a zeitgeist shift happening. It has to do with the spiritual evolution of our society. We are seeking more meaning in our lives because a lot of our basic needs are being met. The universal standards of living have reached a different level. Our expectations around our day-to-day purpose and mission are evolving. Our expectations of who we work with and how we work with people is changing. It’s not a coincidence that people are seeking purpose and meaning in community service, or that we’re seeing the rise of meditation and mindfulness. There is this sort of internal spiritual awakening. It comes back to the theme of evolved human beings. The more evolved human beings become, the more we expect from the organizations we work for and with. If organizations don’t meet expectations, others will build it themselves.

Putting Money Into Impact

Deb: Is this mindset shift also going on in the funding world?

Diana: Investors are also evolving as human beings. With my company twine, there were conversations with evolved-thinking investors. Many investors are thinking on a much bigger level around society and the role of companies. Obviously there is a bottom line but the language is shifting. Again, it’s a cultural moment. Entrepreneurs and investors are becoming more socially focused. Values are being matched. I also think that there isn’t a conflict if you have a solid business model. Creating a highly impactful company needs a viable business model. It’s not enough to be a nice company that says they want to make a difference in the world. The most interesting companies right now are the ones that are able to become a billion-dollar company, while doing the right way. It’s how we work within the rules of capitalism to do the right thing for people, communities and humanity.

Looking Forward

Deb: What’s your greatest hope for the future?

Diana: I’m going to shift the question a bit. If I could have one hope for everyone in the world, it would be for them to practice turning inward. I believe that if everyone turned inward and spent more time seeking to understand who we are, it would greatly help humanity. It comes full circle back to the Confucius quote to start inside and go out. Sometimes we jump too quickly to say, let’s go change the world. If we haven’t worked out all the internal things, how can we help others? The internal work of self-love, self-trust, self-compassion is the foundation of every single piece of how we serve our community and how we serve humanity with integrity.

Companies are the same as people in that way. Companies are built with integrity from the inside-out so they must also turn inward to be able to serve their communities or the larger humanity. You can’t have a company all of a sudden proclaim that they are going to deliver a product that makes their customers’ lives better if they’re not investing into making their employees’ lives better.,. It’s so clear when a company is rotten from the inside out. It never lasts. If companies turn inward and align themselves according to their values, they can understand what they stand for. Every single action that we take has to be in alignment on a daily basis with what we stand for, because how you do anything is how you do everything. This is what I mean by turning inward. There can be too much of an external focus that deflects from our true purpose. With internal focus, we get a little bit closer to the core of why we do what we do.


Leadership is the fundamental ability to behave with humility and wisdom, to engage authentically and to inspire others towards achieving a greater purpose. Diana models service leadership behavior and gives us hope there are more entrepreneurs like her out there, founding and running organizations. 

A new leadership style has begun to emerge. Leaders are beginning to cultivate a deeper understanding of who they are as individuals and what they value. Knowing who we are and what drives us is critical for creating human-centric businesses that serve. The deliberate practice of self-awareness gives us a greater sense of our place in humanity. This inside-out perspective allows us to serve others, our communities, and humanity.

Engage a human-centric perspective

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