Champion Story 19 | Neil Wainwright
Recorded on December 17, 2018
Biography: Neil Wainwright is the Founder & CEO of UpHabit, the Personal CRM app that helps you build stronger relationships. He has more than 30 years of technical engineering experience and has been an entrepreneur in building and managing businesses for over 25 years. He has a strong business leadership background and broad technical skills cultured through firms he has founded and through senior management positions held at Nortel Networks, Lotus Development, and IBM.
Neil is a professional engineer and holds a BSc in Electrical Engineering from Queen’s University in Kingston, Ontario. Neil has bootstrapped his way through multiple businesses and has raised private equity/VC investments. His last business was quite successful and recently led to a significant exit. Neil is now actively involved in another startup and in coaching and mentoring the next generation of Canadian entrepreneurs.
Thank you so much for making the time to do this. I remember when we first met, which was at Mike [Brcic]'s dinner. I was just really touched by your sincerity and the conversations we had about mental health.
Thank you, yes. It's something we don't talk about much as a founder. And founders are supposed to be, you know, perfect in everything. We're supposed to be running everything. We're supposed to have infinite, you know, capacity to do anything. And that's really not the case. And you know, the interesting thing about being a founder is it's a very lonely job.
Typically, all the problems flow in one direction and that's towards you. And as much as people might think that it flows away from them, the reality is that it's always our fault. When something hits the fan, it's always our fault and something we have to fix. And we have to do that going in. You know? For younger founders, it is a 7/24 job. There's no such thing as work-life balance in a founder's life.
Most times, when you're leading the business, you're going to fail. If your whole life is in this business that's failing, it can be really traumatic from a mental health perspective on you. To watch something you've nurtured and had such passion for years literally crumble around you.
As a founder, I resonate with that. That was one of the biggest shocks for me, earlier on in my journey. How emotionally tolling it can be, given the hours and sweat we put into it. It's basically like your baby or your child.
And you're raising it.
And it's a tremendous loss when it goes.
My first business, I would probably pull an all-nighter every week. And you know, it takes you two days to recover from that, you know? I still did it because I could focus and concentrate, you know, at two, three, four, five, six in the morning when no one was around. Or in the office or, you know, trying to reach you.
It takes a toll.
And I've seen a lot of founders and friends, you know, sometimes they lose the business. Sometimes they can lose their houses. Sometimes they can lose their retirement funds. These are all things that are pretty dramatic in a person's life.
And, there's something mostly unique to founders. Because we're the ones that are signing the personal guarantees. We're the ones committing a lot of times our entire net worth to the business. And if that fails, there's usually no plan B.
I just appreciate your realness; it's something we don't talk about enough. Especially people who might not be founders, but dating one or has a best friend who is one, don’t realize the pressure and how intense it is. Especially when you're choosing to go all-in. Because you're trying to make it work.
Yeah. And in my case, my wife is really supportive of me being a founder. But she knows what it's like. She knows my mind is always spinning thinking about the business. It never shuts off, you know? And my last company, I'd wake up at two or three in the morning and just start writing emails because I had clients around the world.
This is my eighth startup and when I started my wife said, “We are going to have a good balance in our lives. We can do this as long as it doesn’t affect our travel, our daughter.” And I mean, that's one of the things that I have that's a luxury because this is my eighth. I sold the last one for quite a chunk of money, so I have that flexibility.
And when you're a younger founder, and that's why I spend a lot of my time now coaching and mentoring younger founders, you don't have that luxury. It's always going to be a grind. And making sure you're prepared for it, ready for it, know how to handle it.
The pressure of being a founder affects your interpersonal relationships, you know? It’s going to be stressful and if you take that home with you, it will affect your relationships with your friends and your loved ones.
Having the right people around you that can watch that and know you're going through. People who can be supportive of you when you're not the best is important.
Yeah. In my circles, many of my friends [who are founders], we talk a lot about relationships. Dating, family planning, how can we make it all work. And it’s a constant struggle to do both.
Often, founders are wondering like, “How do I balance?” How do I, as a founder, have good relationships with my friends and family?
Yeah, that's been really critical for me and my success. I remember going to MaRS for a presentation and there were some VCs at the front of the room. One of them is an old classmate of mine, Scott Bonham. And someone in the audience asked about work-life balance and how do you maintain that in the startup environment.
Scott's a wonderful guy and he's given back a lot to the community as well. His response was, “You never talk to a VC about work-life balance.” Venture capitalists, you know, they want people working. They want them to be 7/24, never-taking-a-breath kind of thing. Because rightly so, they've given them a lot of money to create a unicorn.
Yet work-life balance, you really need it actually.
You know, I don't think you can be performing at an optimal level if you're so buried in things and so stressed. Not sleeping and working, you know, seven days a week and everything else. You need some type of balance that fits you and your personality and your needs. Otherwise, it will consume you and it will not be the most effective thing for the business.
I mean, for me and my last business in 2015, I raised some money from private equity. And over the span of 17 months, I actually sold out control and all of my shares. That was a very stressful time for me. It was probably, I had some of the worst work stress of my entire career. But I felt pressure because I had accepted someone's money on the understanding that they wanted to create something massive and bigger.
I applied it to myself because I wanted to deliver for them. And you know, the other interesting thing from a founder perspective is that although they're in charge of everything, they don't have full control of their business. I mean, you know, the employees could leave. The markets could change dramatically. Google got into your business, guess what? You're going to get wiped out.
Lots of things can happen that are out of their control, yet ultimately affect their mental health, their ability to sleep at night, and their ability to feel good about themselves and what they've achieved.
Thank you for being real with me about your journey. I know you are very accomplished as a founder, but I'm so curious to learn more about you as a person. How would you describe yourself?
That's funny. Like, we always have this opinion of ourselves that's probably really far divorced from reality. But for me, you know, I really want to do the right thing. That's one thing that's been a constant throughout my entire life.
I always want to be considerate of the people around me, the people that I work with or work for. I don't think I've ever screwed anyone over in my entire life. It's just not in my nature to do that. I will bend over backwards to make sure I don't do the wrong thing for someone. And if that ever came to pass or I ever do something where I think I made a mistake, I obsess over fixing it, right? You know, if I've impacted someone in a way that I really didn't want to, then I'll do everything in my power to make it right.
I want to do the right thing for others. Did I do it the right way? What have I done for others? You know, the money has worked out over the years. It's been really rewarding from that perspective. But I think the strongest companies are those that are built on a strong culture and a strong set of values. You know, get back to the VCs for a second. I went and visited Andreessen Horowitz a couple of years ago. They're in Silicon Valley. And that company is built around an obsession over the founders.
And it was really eye-opening to me. Because I hadn't heard of another VC that was like that. And still haven't heard of another VC that's like that. But they are all about the founders. They will wrap an entire founder, an entire team around a founder, to help the founder with the things that he or she may not be strong in. Just so they have a strong environment in total. I think that's more the exception to the rule. But it was really eye opening to see them.
And they're obviously very successful, they invested in Facebook, you know? That was one of their big wins. And they've stayed through Facebook all the way through. And some of the troubles they're having now, they've been supportive through the whole process.
That’s a wonderful example. I hope more people look to Andreessen Horowitz to support founders. Founders can do so much more when we provide them the support, especially the people, to see them through.
You mentioned about strong culture… When I speak at events, a lot of people [team members] approach me saying that they can’t relax because of their leaders. The founders and the executive team have a huge impact on what values are chosen and how they are implemented. It really affects employees.
Number one, if you want to know the true values and culture of a company, you have to look at the founder and the CEO. Because it all flows down from him or her. You can't have a culture on the wall, a culture defined on the website be true, if it's not aligned with the founder's values and beliefs.
If someone's looking at, for example, you have three job offers, which one do you take? Find the founders and CEOs that you really believe in. And then, if you align with their values, you'll have a great time. If your values aren't in line with the company, it doesn't matter how much money they offer you, it's going to be an uncomfortable and bumpy ride. You're not going to enjoy it.
What are your values as a person?
To always be giving back, to be kind. To be, you know, to be smart about what I'm doing.
And to continually learn. I'm doing more and more of that now. The older I get, the more reading I do. And I think about how much better I would've been as a CEO all along if I had read more, you know, and learned more.
And the challenge with business when you start a business, you get consumed by it 7/24. You don't have time to think. And, you know, there's a saying “don't work in your business, work on your business”. Very few young startup CEOs have the time to do that. They're just buried in everything that needs to happen.
What are things that have helped you discover your values? How have you discovered what's important to you?
You know, a lot of it comes from within. One of the things that I would suggest because this didn't exist when I did most of my startups… There's such a huge potential network of advisors out there. And these are not people that want 1% of your business to advise you.
These are people that are giving their time freely to advise you because they like you, because they want to help you, because they've been through the journey, and they want to help you along yours. Seek out a number of those people that could potentially be advisors for you, to bounce ideas off you. I remember a group called Peerscale, which is about 100 software COs, about 100 software executives, like C-levels.
And you know, it's a great group. I probably made an extra $5 million dollars on my last exit, because of that network of people I had to advise me. You know and it's worth it to have these advisors. It'll help you scale your business a lot faster. You know, I learned a lot from my peers.
That is interesting that you speak about advisors. Often times, we are giving away our equity to get them or we get desperate and grab whoever is available. We could use more dialogue about what it means to get a good advisor.
I mean, what's your perspective on that? What do you see now?
Founders need to lift their heads. They need to talk amongst the community. They'll build a network of associates or people that they feel that they're comfortable with.
Strategic advisors, I don't want any monetary return for giving my time. At that point, I'm not volunteering, I'm just consulting. I've met with startups where they're like, “Well, we want to give you some equity or you know, I'll sign this thing.” And when I sign the thing, it says that means they own every idea I ever tell them. And I'm like, “Well, I'm not going to sign that for 1% of a startup that doesn't have any revenue.”
I said, “I'll just meet with you and give you all kinds of advice.” And some of it might make sense or just to hear you. Because they might not want advice. They might want to just tell their story and then get validation on it. But if I'm getting something in return, it seems like I'm just consulting them on it. Finding these kinds of advisors.
Thankfully in Canada, we have a much more supportive infrastructure.
It’s not as cutthroat. So we're trying to lift everybody up. There are people out there, lots of people out there that are willing to offer their time. You've just got to find them. But that means lifting your head up and starting to network and talk. Say hey, “I've got this issue.”
It's just about asking people. Being open to asking people. Also, is there any way you avoid raising capital? Because when you raise capital, you start giving away the most expensive thing you have in the business, which is equity. You'll never get that back. It can create a lot of problems down the road.
What do you notice is the hardest part for founders in terms of mental health?
In my case, I felt responsible. Like I needed to earn them [my investors] a lot of money. I had to create a bigger company because I accepted money. And yeah, it puts more pressure on you. You know, I accepted a little bit of money, then I accepted a little bit more money.
Then I sold control. And I was fired three weeks later. And I ran the business for 14.5 years.
But that was their right, they paid for it. And then a little bit later, they bought the rest of my shares and I was 100% out. But you know, they bought the business. They could do whatever they want.
And the frightening thing for a lot of founders is their whole sense of self-worth is tied up in the business. When you get canned after 14 years, you can crash really hard. I was fortunate in that because it was my seventh business, I knew there was life after.
And you know, my wife's response. You talked about having friends and family around you. When I told her that I had been fired, she said, “Great, you're going to the gym tomorrow.” That was her reaction.
Then she said, “You're going to, you know, get healthier.” Because she wants me around for a long time. After that, my stress disappeared almost instantly. Like I said, I had probably the most stressful year of my life preceding it, so it was good. I had a large capacity, I have a large capacity for stress. But I probably hit my maximum in the fall of 2015.
You're here now.
Most founders, they don't have these really big, you know, successful exits. And the reality is, a lot of them are going to have unsuccessful exits before they have a good one.
And then everybody says you're just an overnight sensation. You're so successful, you started a business, and sold it after three years or two years or whatever. And I'm like, no, no, no, I spent a whole career before that failing before I had that success. I was going through some pretty painful lessons for the previous 10 or 20 years before I got to that point.
Typical businesses that are around for like 8, 12, or sometimes 15 years before they're sold. Until we have these conversations about mental health and everything else, people aren't really going to understand.
Given everything that you are speaking about, what can founders do to protect or maintain their mental and emotional wellbeing?
Well, number one, they need to know that it's normal. These waves, the highs and the lows. You're feeling like you're overwhelmed or you don't feel worthy of what you're now being asked to do. Or you're passionate, so you're passionate about your business. You get angry and upset.
And these are all normal things that they should know that every CEO is going through. Especially in a high-growth business. They're all going through those kind of waves. If you know it's normal, then you're like, “Oh okay.”
You can actually, you know, get to a better self-awareness where it becomes less dramatic. So, the highs and the lows or at least the lows don't go down so low. Because the more balance and perspective you have in your life, then the more you can see the overall arc of what you're doing. The less, you know, the shocks are going to affect you.
Yeah. I mean, when you spoke of Peerscale, I've been so grateful for communities like that. We're starting to see more of these kinds of groups where we can share in a safe and confidential way.
One last question. When you think about us as an industry, what can we all do together to move mental health forward?
We just need to strip away the taboo about talking about it.
You know, that's what a lot of it is. If people were open to talking about it, if they didn't have to be afraid about it, then I think a lot more would happen around it. My daughter volunteers at Jack.org, which is about youth mental health. And it's a wonderful organization, but it's literally about conversations.
They have this thing called Jack Talks where on university campuses, there are meetups where they just talk about mental health to the university environment. And they'll have these students that are ambassadors. But they'll get up and they'll talk about their own journey with mental health and what it means to them and where they are with it now.
When it comes to founders and their mental health, it's exactly what you're doing. You're starting the conversation about it.
Thank you so much for being a part of this and your generosity.
My pleasure.