Operator Spotlight: UpLift Co-Founder & CTO Laura Butler

Looking for practical help and advice on an operational area that may be outside your realm? Each month we spotlight one of our talented operators, who’ll share their expertise and offer insights and ideas that may help improve your own operations. This month we spoke to UpLift’s Co-Founder & CTO Laura Butler.

You spent 22 years as an engineer and technical fellow at Microsoft during some incredibly pivotal times. How did your time at Microsoft help you develop as a leader? 

LAURA: First, I got to work at the company during an incredible time in the early 1990s when mission was so front and center to everyone. We were changing the world by expanding the set of people who had access to top-notch tools and information through devices by orders of magnitude. I learned the value of a great mission and vision; they energize people. They help teams through tough times to know why they’re slogging and how it matters. They guide more coherent decisions, features, and products. 🔭 

Second, I got to see great leadership in action during the early days of Windows and Office. People such as Brad Silverberg, Jodi Green, David Cole, Rich Tong, Julie Larson-Green, and many more. Space is infinite, right? ♾ The set of stuff that works is the interior of a cube and that’s finite. Unfortunately the set of stuff that doesn’t work outside that cube is infinite. That’s to say that learning what not to do and when not to do it only goes so far; being able to observe how incredible people operate and how they solve problems is huge. 🕵🏾‍♀️

Third, rage-quitting after a reorg in 2000 was a transformative moment. I had to grow up, figure out what really matters to me, and develop a philosophy. You can’t be a good leader, especially an engineering leader, without these things. When you’re an engineering leader, part of your job is to engineer the engineering culture. Before I quit the first time, if I’m being honest, my approach to leading/managing was like a refrigerator light 🔦.  Everybody around me was there to turn on when I opened the door because I needed something, and it wasn’t my fault if they were illogical or unable to understand my genius.  

You had a hand in the user interface (UI) of many of the Microsoft programs and apps we use on a daily basis. Looking back on it now, what was the environment like for engineers? 

LAURA: Computing resources were very tight in the 1990s. 🧮 You couldn’t work on the UI and not be deeply familiar with memory usage, CPU, I/O, and more. Rendering used math front and center:  rasterops and vectors and sets and matrices. Everyone, regardless of specialty, had a solid fundamentals base. There was less silo’ing, more respect, and a lot less “you’re just a front-end engineer, while the real programming is back-end services” kind of elbowing. 👩🏽‍🔬

You absolutely had to be able to debug up and down the stack to make things work, and work well, in Windows ‘95. On top of that, you had to intuit what app developers were doing and how they were doing it so you could solve compatibility problems your changes caused. (You would not believe the number of bugs that increasing the width of a line from 1 to 2 pixels can cause. 🐜)

Because releases were slower and computing resources were tighter and the cost of correcting errors in shipped software was higher, engineering teams invested a lot more in design and architecture, documentation, tools, and training. It was part of the job to keep things up to date, and we had support from technical writers, product support, and others. 📝

Today you can try and test things in minutes, and if you don’t cut corners, you can right roll back the changes in minutes when you find out how badly you’ve broken things. That’s wonderful; it gives such space and freedom to experiment and learn. But the flip side is that the engineering rigor muscles have atrophied. Distributed services have layers of resiliency and robustness — as they must — but some of that is at the expense of debugging and truly fixing problems, rather than putting band-aids on them. 🩹

Here’s a photo from the launch of Windows ‘95 with some state-of-the-art laptops. We look like a New Wave band!

You founded UpLift Group in 2020. Tell us about UpLift and what prompted you to start a business. 

LAURA: Thank you for using the word business! I’m proud that we have revenue from people who aren’t related to us, don’t even know us, and choose to pay us. 📈

First let me explain what my startup is doing. UpLift Group is building the CarFax and Consumer Reports of condos. We want happy owners in healthy Homeowner Associations (HOAs). Our mission is to provide quality information and accessible expertise about condo and townhome HOAs for individuals. 💪

So how did we get here?

Carol, my co-founder and CEO, and I knew in 2019 we wanted to found a company and we wanted to do it old-school: bootstrapping and starting from square 0 for the learning and experience.🛠  

As part of making changes, I Marie Kondo’ed my life. I had a house that was too much work to care for, plus had tripled in value, so I sold it and bought a condo. Condos are supposed to be easy, right? They make great homes for people who don’t have the time, desire, ability, or money to take care of a stand-alone house. They offer amenities, security, logistical efficiency, and access to opportunity and culture in urban areas. 🌆

I almost bought a condo that I would have regretted immediately due to pet restrictions 😿 and an upcoming special assessment. 💸 I fell in love with the space and didn’t even think about the HOA. I didn’t know what I didn’t know. HOA docs are immense and inscrutable, but they are also often incomplete, out of date, or just plain wrong. So even if I’d had a clue, I would’ve had difficulty establishing the facts. 😱  

It turns out that HOAs are hard. Understanding them requires mastery of arcane finance, governance, and maintenance. Fortunately Carol is a world-class expert on condo/townhome HOAs. She’s owned many condos herself and served in every board position. Plus she’s an economist with a background in data science and econometrics, specializing in utilities and public policy. You couldn’t manufacture a better person in a laboratory if you tried. 🧪  I’m now a happy owner of a different condo because of her. 

So a lightbulb went off 💡 and we decided to focus our startup on HOAs. The more we dug in, the more convinced we became that there were huge gaps, huge problems, and therefore a huge opportunity to help people and create value. Our core service today is a Resale Review, scouring the indigestible stack of material a buyer gets about an HOA as part of resale disclosure, analyzing it, extracting what matters, and making it easy to understand. We help buyers and their agents decide whether to go through with a purchase, give them data that helps with offer negotiations, and ensure they’re prepared to be owners. We provide peace of mind. 🧘‍♀️

As a bonus, here are a few ideas we didn’t pursue. If somebody out there wants to run with one of them, hit me up for details and possibly an angel investment 🙂

  • Patroness 🎨🎻… a way to support artists, actors, and musicians by letting them stay for free in your home, buying them meals, or hosting an event in exchange for tickets.
  • Carma 🚗👍🏼… a mobile app you can point at a license plate and then send thanks or a small gift to the driver when they do something nice (like let you out of a parking garage on a busy street)
  • Lo-cat-or 🚁🐈… rentable drones with infrared, microphones, speakers that maybe also can emit treats you can use to find your lost pet

The number of technical women founders and CTOs is on the rise. How has the landscape changed for technical women over your career? 

LAURA: It’s come back around to where it started, even better, and that’s a good thing. When I joined Microsoft, there were more women in programming, more women engineering managers, and more women in senior positions. There was no engineer cookie cutter stamping out the same shape. The industry was creative problem solvers and misfits figuring things out that hadn’t been figured out before. 👩🏿‍🎨 

Somehow it got middle-aged, pompous, exclusionary, stratified, and unwelcoming around 2000. 🏹🗡 I’m not sure where the zero-sum winners-losers kind of behavior came from. Insecurity must have been a factor. Maybe getting more removed from real purpose and humans was a factor too. Programming became a priesthood and cult of its own, instead of a toolset. 🏛  In any case, this impacted a whole lot of people besides women. Who’d want to study computer programming if it was all or nothing, you didn’t think you could pursue your other interests, and you didn’t look like the people already in the industry? 🚫

I love how less binary and more quantum programming has become in the past 5-10 years.  Open source, SaaS, and low-code are here to stay. If you have an idea, there are multiple ways you can build it. You don’t have to get a CS degree. The whole “technical” vs “non-technical” distinction is less relevant and clear every year, which is fantastic. It’s ever more about making things to solve problems and solving problems to make things, as it should be. 🤗

In your opinion, what are some ways the tech and venture industries could do a better job of empowering the next generation of diverse leaders?

LAURA: I feel like the “adventure” isn’t as front-and-center with tech and venture as it should be. Of course there is risk. Nothing ventured, nothing gained. But risk is something you manage with action like support and advice, not just assess with data. The point of risk is reward. Following the pack and staying safe are not how you win.  They are defense not offense. 🥅

Tech and venture folks should examine Cirque du Soleil, martial arts, ice skating, gymnastics, rock climbing, and skyscraper construction. Case studies in these areas should be taught in business school. All these areas require failing a lot and are arenas where failing can be catastrophic. So rationally they invest in safety equipment and practice over and over again handling errors and problems to recover as safely as possible. Tech and venture ought to do the same and build virtual harnesses, trampolines, mats, ropes, self-arrest techniques, and rope teams. 🤸🏽‍♀️

Why does this matter? Because great management and leadership take practice and development. And underrepresented groups have less room to fail. More visibility, more pressure, less resources, and fewer tools to use to mitigate slips and falls = less chance of succeeding and more damage when problems arise. If the industry truly wants to invest in people, it should invest in the equivalent of safety equipment and padding to minimize the bruising. 🦺

AOC often talks about the skills she picked up as a bartender, and others talk about what they learned working retail. What were some of those formative jobs for you?

LAURA: I went to college young, plus I was a bookish nerd, so I never had a real job before joining Microsoft as a summer programming intern in 1989. Then I got paid to sit in front of a computer with air conditioning, play Tetris, and blow things up with dry ice inside of plastic bottles, all while getting unlimited free soda and snacks. It was awesome! But I didn’t learn practical things. Between school and Microsoft I was in a cocoon. 🐛🦋

More practical knowledge and experience honestly came after I left Microsoft the first time in 2000. I was fun-employed for 6 years and decided to try things I had only read about.  Adventure travel and cooking were really formative. The former because of a mindset and skill set that carry over so well to innovation. You don’t know exactly where you are going and there aren’t paved superhighways. 🥾🗺 So you need to figure out how to go the distance sustainably and you better enjoy it. The latter requires logistics by restaurant staff at a level that puts engineers to shame. Peaks are crazy high, time is tight, it’s got to be a personal and customized experience, and it’s emotional for your customers. 👩🏿‍🍳🔪

So if your engineering team is complaining about how hard it is to get a feature done and shipped on a schedule, have them spend a Friday night as a prep chef or a line cook at a restaurant that handles a lot of pre-theater traffic. 😰

What’s your secret super power? 

LAURA: Active contrarianism. If you need to lead a rebellion and overthrow an evil space empire, I am your princess general. 👹🌌👸🥊

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