Telling a Startup Story | Cindy McLaughlin at Envelope

In part one of my conversation with Cindy McLaughlin, the CEO of Envelope, she talked about how her startup helps developers navigate the complexities of zoning laws, and the unique partnership approach they employ in their business model.

In this second part of our conversation, Cindy tells us how she’s learned to work through all the apparent catastrophes of running a business, and how she believes a great CEO must be a great story.

More information:

Cindy McLaughlin is CEO of Envelope, a real estate acquisitions analysis company that uses zoning- and AI-driven software to search for, visualize, and run scenarios on urban real estate value potential. 

Prior to Envelope, Cindy held CEO and President roles in a range of technology companies, from fashion technology to education technology for prisoners.  Cindy has an MBA from MIT/Sloan, a BA from Mount Holyoke College, and spent 2 years in Congo as a Water/Sanitation volunteer for the US Peace Corps.

DISCLAIMER: Below is an AI generated transcript. There could be a few typos but it should be at least 90% accurate. Watch video or listen to the podcast for the full experience!

Cindy McLaughlin 0:00
It’s really always, always always about storytelling. It’s about painting a picture, it’s about showing people what the future is going to look like once the company succeeds.

Alexander Ferguson 0:20
In part one of my conversation with Cindy McLaughlin, the CEO of envelope, she talked about how our startup helps developers navigate the complexities of zoning laws and the unique partnership approach they employ in their business model. In the second part of a conversation, Cindy tells us how she’s learned to work through all the apparent catastrophes of running a business and how she believes a great CEO must be a great storyteller. Cindy, I’m excited to continue our conversation now hearing a bit more about your story, your journey. Tell me where did you begin? Were you always a New York? New Yorker? Or what’s your journey been?

Cindy McLaughlin 0:57
Like? Sure, I grew up on a tree farm in Western Massachusetts. Um, I lived on 27 acres of mostly woodland. So I was a Woods kid, you know, I played in streams and caught frogs and ran around our meadow.

Alexander Ferguson 1:18
And now it’s changed a lot. Do you dislike the the nature of outdoors? Like give me the urban or how has it changed?

Cindy McLaughlin 1:24
No, I love the nature and outdoors. And it calms me down, and it brings me peace. But I love the intensity and movements and complexity of cities like New York.

Alexander Ferguson 1:39
For you that your journey, this is not the first company that you’ve led. That’s right. That’s right. Talk to you about what’s this journey been like? And how do you get to this point where now you’re CEO of envelope,

Cindy McLaughlin 1:50
I did my MBA at MIT back in 2000. And I focused on technology strategy business, started a company with one of my favorite strategy professors just out of school, which immediately failed. But it gave me the understanding that like, regular people can just go do this. And so ever since I’ve been starting, or helping to lead or on the senior teams of other people’s tech companies. And I’ve developed the idea that running companies has, in many ways, nothing to do with the industry that they’re in. And it’s a little heretical, but I see the same patterns, the same, the same things work and don’t work. leading companies, regardless of which industry they’re in. So this is about groups of people getting together to get behind a vision and execute on that vision. And it doesn’t matter if it’s b2c, or b2b, or in fashion technology, or in prison technology, which was my most recent company. Or in real estate technology, which is where we are now,

Alexander Ferguson 3:13
what’s a difficulty that you’ve had to face maybe recently, in the past several years that you were able to overcome, but another entrepreneur could learn from.

Cindy McLaughlin 3:25
So I’m going to answer it a little bit more generically, I’m going to say that my natural tendency, when I run up against a problem is to catastrophize. And say, Oh, my God, I’m never going to get through this, this is going to be awful. This is going to be the downfall of my company, or the downfall of my career, or, you know, the end of the world. And my husband always tells me, take a deep breath, and work the problem. And so, you know, a million things have happened. COVID happened, which was, which felt like a catastrophe for a little while. And then it felt like an opportunity. And so, you know, working the problem, just taking a deep breath, putting one foot in front of the other, trying to see the big picture, and solve the little problems along the way, knowing that nobody knows what the answer is going to be, has led me through a lot of ups and

Alexander Ferguson 4:27
downs. Can you share anything about that first initial, whether it’s this company, or a previous one that how what tactic we’re able to apply to help get that kind of first beginning with the first couple clients?

Cindy McLaughlin 4:42
It’s really always, always always about storytelling. It’s about painting a picture. It’s about showing people what the future is going to look like once the company succeeds. And if you can do that effectively if you can show people the future And if it’s a future that they’re into, they will get behind you. And I think we’ve been very lucky envelope has been very lucky in that we’ve got a visually cool product we’ve got, we’ve been able to paint pictures, even as the company has twisted and turned, you know, we haven’t always understood what our business model is going to be. But we’ve been able to paint a picture of a future that people find appealing. And I think that’s a that’s a strength of ours, a lot of it is emotional, a lot of it is thinking about. In a perfect world, what would you like to see happen? You know, if there were no obstacles? What would what’s what’s utopia. So we’re doing a lot of storytelling right now for the city of New York, which has many obstacles. But in a utopia, where we’re biking and walking everywhere, all the time, and we’re seeing our buddies in outdoor Wi Fi cafes, and we can just bring our laptops and work and there’s no friction. It’s a very easy story to understand with some visuals. And so I think having, first of all, being able to understand what you personally would like to see, and then having a really good designer to help you draw help you show visually, what that’s going to look like. And being able to kind of guide people step by step toward through how you get there is, is the way to do it.

Alexander Ferguson 6:46
Looking forward, obviously, COVID is a big piece, but what challenges and difficulties you see moving forward, you’re going to need to overcome in the next two, three years.

Cindy McLaughlin 6:55
Yeah, you know, the waves of COVID will be interesting. We always operate in the worst in a worst case scenario, you know, outside with the story we tell is always about, here’s the vision. And then internally, we organize around the worst case scenario. So what happens if nobody can leave their homes from September on, you know, from September to next July, because we don’t have a vaccine that works, because we’re getting the second and third and fourth waves of COVID. Um, so I think the challenges are less about what’s going to happen internally at envelope and more about what are the things that we can’t control? And how do we set ourselves up to get through them. And so that’s a fundraising problem, it’s a, I’m making sure that the team has the long game in mind, and that they’re building toward the long game, even if we’ve got a year of, you know, just a building, and not actually buying real estate, that it’s possible that that may happen. Um, so yeah, it’s a it’s again, it’s like telling a story and making sure everyone’s behind

Alexander Ferguson 8:10
it. Is it difficult for you to keep that, that communication both internally and externally? And how have you how have you execute on that cuz obviously, Team keeping the team in line and ready and still fired up? And your, your partners and your clients, your vendors? How have you done that communication?

Cindy McLaughlin 8:28
Yeah, um, so part of it is just I started by hiring people, I really trust hiring grownups hiring people who are self motivated, and you know, they have their own kind of internal Northstar for what needs to get done. Um, I then have a very transparent management style in house. So I keep my team very informed about what’s going on with me with a company, um, you know, with financing, so they’re very much in the loop. And every time we have these discussions, we reiterate, here’s where we’re going. And so, you know, bear with me in all the you know, and all the bumps in the road there would be through the roller coaster of the startup. And we always finish every conversation by saying, and here’s where we’re going. And let’s like put our heads down and stay the course and get there

Alexander Ferguson 9:31
for you to to calmly lead your team and your company forward. Where have you gotten your insight and learned in the past? What books or audiobooks or podcasts have you gone to a read that you enjoy?

Cindy McLaughlin 9:46
Well, I almost never listened to business stuff. You know, I’m, I tend to be more intuitive on the business side rather than you know, I’m not sort of constantly reading or listening to business books and podcasts. I listened to pod save America almost every week. I’m very into politics right now. And that’s kind of my escape from business. Um, you know, when things seem under control with the company, I slip into politics mode and things do not seem under control on the political side.

Alexander Ferguson 10:24
So being able to listen to something else outside of business, gives it a kind of a fresh break, and then other fictional items or stuff, do you able to kind of take back as well? And I do find that’s helpful to get a different mind shift.

Cindy McLaughlin 10:38
Yeah, you know, as I mentioned earlier, there are so many similarities, I found similarities in running companies across all of the work I’ve done. And kind of integrating all these lessons learned is part of I think, how I’ve become a better leader over time. And so understanding what’s going on in politics, understanding a little bit a little bit about the history of our country, and listening to a podcast called slow burn right now, which was, which starts with Watergate. And the most recent season, which I have not yet listened to is about David Duke and the rise of white nationalism. So being able to hear stories, you know, hearing stories about how history has repeat has repeated itself over time, and how things have differed or how paths have diverged based on a little decision that somebody made or based on somebody’s personality, has been fascinating, but also it helps me learn how to think about those decisions when it comes to my company.

Alexander Ferguson 11:54
Last question I have for you, what kind of technology innovations do you predict we’ll see in the near term next year. So and, and the long term 510 years,

Cindy McLaughlin 12:04
I think that there are innovations in transportation and transit that are going to curb management that are going to change the face of cities. So things like individual parking, space, pricing, and pricing by the second, you know, we’re pricing by the minute. I’m essentially demand based pricing. Things like micro mobility, going to autonomous protected pods, right, that are all weather where people can zoom around in a one seater that is less dangerous than, say, a moped but serves the same purpose and is applicable across cities that are weather constrained like New York.

Alexander Ferguson 12:57
That concludes the audio version of this episode. To see the original and more visit our UpTech Report, YouTube channel. If you know a tech company, we should interview you can nominate them at UpTech Or if you just prefer to listen, make sure you’re subscribed to this series on Apple podcasts, Spotify or your favorite podcasting app.



YouTube | LinkedIn | Twitter| Podcast

Grooming Your Startup | Erinn Valencich at StyleRow

Making the Cloud Rain | John Jahnke at Tackle