From Big Tech to Small Business: A Conversation with Laurie of māk and Tara of Watershed Cafe

Laurie is the owner-operator of māk, a creative drop-in studio with regular workshops that has become a favorite third space for friends and a top pick for couples and groups.

Tara is the owner-operator of Watershed Cafe, which has quickly become one of Oregon City’s most popular and beloved hangout spots, and the first stop on many tourist trips and family visits.

Both business leaders have something interesting in common: until recently, they both had demanding careers at huge tech companies, Microsoft and Amazon.

I sat down with Laurie and Tara to ask what the journey from high-tech spaces to Oregon City third spaces has been like, and what we can learn from it. (A third space, by the way, is somewhere that isn’t your work and isn’t your home, but these two might have their own ideas about what that means.) 

— Matthew 

What was the moment you knew you were done with tech?

Tara: It came slowly, and then very quickly. Over time I realized that what I loved about tech was the people I worked with. When that changed, when the people around me no longer aligned with my values, it became very hard to keep doing work that didn’t impact my local community the way I wanted. They say people don’t leave companies, they leave managers. That was my moment. My slow progression turned into a very quick sprint out the door.

Laurie: Mine was similar, but different too. I loved my job and the people there. I was at Microsoft for 20 years, but over the last few years I slowly started burning out. It became less joyful to go in every day, mainly because of a couple of people. I thought, I’ll just power through a few more years and then do something I love and work for myself.

Then I got laid off, so I didn’t have a choice. I really feel like that was the universe saying, “You’re going to hang on here forever, so we’ll do this for you.” I look at it as a blessing. I already had the beginnings of a business plan, so I just fast-forwarded and started moving on it.

What did you give up to make the move, and was it worth it?

Laurie: It would have been easy to roll into something similar, somewhere comfortable where people knew me. But I knew that wasn’t right for me, so I opened my own small business.

I gave up a lot. When you open a small business, you have no income. You’re paying to work. I gave up insurance. I gave up time. I don’t get vacations anymore, or work trips I can extend to go explore. My friends say I’m raising a baby, and it really is like having a newborn. I’m 100% focused on making this work.

But is it worth it? Absolutely. My mental health is better. The decisions I make are mine. There’s no drama, and if there is, it’s drama with myself. It’s very nice to know the outcomes I see are because of the work I’m doing.

Now I have to be very conscious of how I spend money, which makes me deeply thankful for the people who choose to spend their dollars in my space, especially in this economy.

I also gave up time. Working from home, I could do laundry between meetings or pick up my kids during a call. Now I’m lucky to live in the town where my business is, so my son can walk down from school to the cafe. Without that, it would be very hard to be the kind of parent I want to be.

Did you know what kind of business you wanted to build when you left?

Tara: I did. When I was still in tech, my husband saw how burnt out and unwell I was. One day he stopped and asked me, “Tell me the last time you loved a job. When did you look forward to going to work?”

It took about three seconds for me to blurt it out: when I was working in restaurants. When I was a barista, a bartender, seeing people from my community come in every day for their coffee and getting to talk with them. Hands down, that was my favorite job. It didn’t feel like work.

And he said, “OK, go do that.” I guarantee he did not expect the side quest of being married to a small restaurant owner.

I knew what I wanted to do, and because I live in Oregon City, I knew what this community wanted and that it didn’t exist yet. Building relationships has always been central to who I am. Giving someone what might be their only interaction of the day, and making it a positive one, is extremely valuable to me.

Laurie: I didn’t know exactly what I was biting off, but I’m learning fast. At Microsoft, my job was building community within tech. I built communities from the ground up with people all over the world, and I loved bringing people together. But creativity in tech is hard to come by, and I knew I needed to use mine.

Now I get a community that’s a 180 from tech, and it’s local. I don’t live in Oregon City, but I love this community and the direction it’s going, and there was nothing like this here. I wanted a place where people could have a glass of wine, sit down with a friend, and actually do something. A lot of people want more than just going out for a drink.

What did a stressful day look like in tech, compared to now?

Laurie: In a big corporation, there are goals and milestones and constant reporting out. Now that I’m removed from it, I look back at the stress of making the deck and having the meetings and think, that was all so unnecessary. But when you’re in it, it’s very real. The corporate ladder is real. And I never wanted to let down my team, my manager, or the communities I led.

Now it’s just me. I’m ADHD, so I have so many big ideas, and the stress is getting organized enough to do them all. There aren’t enough hours in the day. I’m constantly figuring out what to outsource, what I can afford to, and what has to wait for phase two.

Tara: In tech, a stressful day meant reporting to a room of executives on software that would reach millions of people and affect revenue on a huge scale. Someone very high up, with little knowledge of the day-to-day, would look at my work and say yay or nay. If I didn’t do my job well, an engineering team could look bad. It was very political, sometimes cutthroat, and I had to keep my head on a swivel to protect the people who reported to me.

Laurie: The politics made it all feel pretend.

Tara: Now, in the restaurant industry, the stress is what you’d imagine. Financial, number one. On a good day, a restaurant makes about a 2% profit. Paying my staff a living wage matters to me, and I also pay for their health insurance, both rare in this industry. So a slow day is stressful, though thankfully those are few and far between.

A stressful day could mean we’re out of everything bagels and someone takes it out on a staff member. Or a vendor forgot a delivery and I have to find bacon by 8 a.m. Saturday.

Matthew: Not very political.

Tara: No, these are not political challenges! But it’s a people business. Someone will be upset about waiting half an hour for breakfast on a Saturday, and I have to explain that we make everything from scratch. My biggest stress isn’t my reputation. It’s how someone might treat my staff in a moment of frustration. I’m very protective of my space and my team.

What skills did you bring from tech, and how useful are they day to day?

Tara: At my old company, I spent a lot of time as what’s called a bar raiser, basically a professional interviewer. That taught me to ask behavioral questions. Instead of a hypothetical, I ask, “Tell me about a time you handled a really upset customer. What did you do?” Then I follow up. I do all the hiring now, and I wouldn’t know how to hire this way without tech.

“Fail fast” was also a real thing. On most of my teams, you were celebrated for taking a risk, even if it didn’t work. A lot of businesses get slowed down by needing everything to be perfect. I don’t. If a menu item doesn’t do well, I don’t take an ego hit. I ask: What did we learn? How could we change it? The follow-up questions you ask to ship software translate really well to menu items.

Laurie: A lot of the same. At Microsoft, failing wasn’t a bad thing either. It’s better to find out now, scrap it, and move on than to keep doing something that clearly isn’t working.

My menu is art projects, like Tara’s is food. Sometimes I take something off the menu to change things up and the crowd goes wild: “No, we want to keep that!” Other times I think something will be great, and nobody orders it. All right, we learned. Won’t do that again.

I’m also not scared of using tech in a small business. A lot of small business owners are tech-averse and don’t know where to start. I’ll just dive in, whether it’s my website or setting up automations. And I know who to call when something goes sideways.

The organizing skills carry over, too. I used to schedule product feedback sessions. Now I schedule workshops. Finding the instructor, setting up registration: same rhythm, different tasks.

How are your customers now different from the people you served in tech?

Laurie: They’re just people. People want to be seen, heard, accepted, and part of something. In tech, I brought people together around technology. Now it’s around art and creativity. But it’s not about what we’re making. It’s about the experience. People will remember how they felt and who they were with more than the thing they made.

Tara: People are people. Human beings are wired for connection. Starting with social media in the early 2010s, and then through the pandemic, people started finding community on their phones instead of at the coffee shop, the pub, the church, or the library.

Now I’m seeing a dramatic shift: customers are lonely. They’re craving connection. They’ll remember the latte was great, but they’ll remember how the barista made them feel even more. They can get a latte anywhere. They choose us because of how they feel when they walk in the door.

That’s what the third place really is. It’s not your home, it’s not your work. It’s the place where you feel seen. People will pay seven bucks for a latte without knowing exactly why, but it’s that emotional connection.

What does “third space” mean to you?

Tara: Third places have been around a very long time. Matthew, you’re British. What is “pub” short for?

Matthew: Public house.

Tara: Correct. And what’s the concept of a public house?

Matthew: It’s somewhere the whole community comes together. It’s not about getting drunk. It’s about being with the people who live around you.

Tara: Exactly. Cheers made it a big thing. And I was a teenager in the ’90s, so I’ll date myself: Friends had their coffee house. Seinfeld had the diner booth where they talked about the most ridiculous things. Buffy the Vampire Slayer had a place. 90210 had the Peach Pit, for goodness’ sake! Every show I grew up with had a third place to talk about what was happening at home, work, or school.

Matthew: Thank you for relating that to ’90s sitcom sensibilities.

Tara: I will always bring it back to ’90s sitcoms.

Laurie: Tara hit the nail on the head. One of the best compliments I’ve gotten came at our Galentine’s event, right after we opened. Someone told me, “I didn’t know anybody here, but I felt like I walked into somebody’s living room with a bunch of friends.” It was such an eclectic group, and none of them knew each other, but they all felt that sense of community.

I also hear, “It feels so good in here,” all the time. That’s my why. That’s when I get the warm, fuzzy feeling that this is why I’m doing this.

Tara: One thing I’ve learned: a third place builds a community of regulars, but when a stranger walks in, they can’t feel like the odd one out. Whether it’s your 20th visit or your first, you should feel welcome. That takes intentionality in the design, the customer flow, even how many seats you have. Designing my space to feel welcoming and make people want to come back was a ton of work, and I never could have done it the way I did without my time in tech. Building software that feels thoughtful and convenient takes that same intentionality.

Why Oregon City? Did you look at other places?

Laurie: I live in the house I grew up in, in Lake Oswego. My kids have my bedroom and my brother’s bedroom. My son even had the same teacher as my brother. We go deep. I love my community, but my whole life has been there, and I wanted my business somewhere different. I see so much potential in Oregon City. It’s only 15 minutes away, still in Clackamas County, and I just love it here.

I liken it to a Hallmark holiday movie. I swear, this Christmas I’m going to the tree lighting, because I’m going to find a husband.

Matthew: You almost have the Hallmark story already. She leaves big tech for a small town. Is there a lumberjack waiting?

Tara: I have the coffee shop for you to get a hot cocoa and watch the tree lighting across the street. We can make this happen.

Laurie: Excellent! But really, I love the vibe here. I’ve always built things from scratch. In tech, I built a community from scratch, and now I’m building my own little community here, where nobody knew who I was. It’s a good challenge.

Matthew: Tara, I know you’re a bit of a history buff. Did that factor in?

Tara: Yes. I grew up on the East Coast, where things are older, and I love a good downtown. My family moved to Oregon City in 2020, in the heart of the pandemic, because it’s close to Portland but feels like a small town. There are almost 40,000 people here, but with the bluff and the downtown, it feels very small.

I grew up in a town of 5,000. My dad was the town mechanic, and my stepmom owned the hair salon. I never imagined owning a small business, which is so ironic now. I should have seen it coming!

My dad would drive down the road with his arm out the window because he waved at so many people. Now I go to the grocery store and see someone from the cafe, or run into a regular at another restaurant. Oregon City feels like the town I grew up in.

It was also missing something I wanted to create. You’re not going to strike up a conversation in the frozen food aisle, but you might with the person next to you at the breakfast counter: “Oh, you got the breakfast burrito? Isn’t it so good?” And months later you’re exchanging Christmas cards. Most restaurants here are table service, where you sit in a section and never talk to the next table. So I built a model where you walk in, get your thing, and sit down. You can come back up to the counter, leave when you want, or stay three hours on your laptop. There aren’t many places like that around here.

Matthew: And Laurie, at your workshops everyone sits together, too.

Laurie: For the classes, absolutely. And my favorite part is when people get up and wander around asking, “What are you working on?” and everybody starts talking. At a workshop last night, the teacher walked in and said, “Oh my gosh, this place is crazy!” We had the Happy Hookers, our crochet and knitting group, in one corner, and other tables doing their own thing. It was lively and loud, with everybody checking out what everyone else was making. It becomes a true community.

What would you like to bring to Oregon City beyond your business?

Matthew: You’re both so active in the community, politically and otherwise. What would you like to bring to Oregon City outside of your business?

Tara: I think people don’t realize how easy it is to get involved. I didn’t, until I learned about something that would dramatically affect my business: the courthouse being torn down and a new development bringing residents downtown for the first time in a long time. That’s exciting for my business, but also for me as a person. I believe in people living close together in walkable communities.

It shocked me how easy it was to write a public comment, speak to a city or county commissioner, be heard, and get a follow-up. This is so much better than complaining! They’re thrilled when someone shows up.

It’s easy to be a keyboard warrior, and it’s easy to watch a city commission meeting on YouTube. I wish more people would get engaged, understand how decisions are made, and stop thinking it’s somebody else’s responsibility. That’s my biggest wish for Oregon City.

Laurie: I’d add hearing from the people actually making the decisions. So many people rely on social media: “Well, I heard this and that.” With the courthouse, people didn’t understand who owned it or the why behind the decisions. Educating yourself is so important.

I also want people to understand how important small businesses are. In corporate, I supported Small Business Saturday, but I didn’t really understand the impact until I became an owner. When you spend money with a small business, they spend it with other local businesses: the printer, the sign maker, the marketing person.

And there are ways to help that don’t cost anything, like liking or resharing a post or leaving a review. We’d love for people to come in and spend money, of course, but those simple things matter so much too.

Midtown especially needs more love. Main Street has DOCA and all the great work happening there, but there are so many businesses up the hill. I’m always looking for ways to get people to hop on the elevator and visit us up there.

What does success look like to you now?

Laurie: I’m still figuring that out. We often think of success as a financial number, but I’m coming up on my first year, and focusing on money right now would just be depressing.

Success is watching people walk in and seeing their eyes get big. It’s hearing them tell their friend or mom or sister on the way out, “That was so much fun.” It’s people who come for one project and stay three hours. It’s someone saying, “I’m not creative, I’m just here for her birthday,” and then leaving with a creative masterpiece. I’m finding success in the little things. I have big dreams, but I can’t call those successes yet.

Tara: At Amazon, the number one leadership principle was customer obsession. It sounds a little manic if you don’t know the concept.

To me, it means understanding your customers so well that you don’t just meet their expectations, you delight them in ways they didn’t know were possible. If we do that for one customer a day, we’ve succeeded.

Here’s an example from yesterday. A staff member came back from leave, and one of our regulars, who sits at the bar every single day and orders a 16-ounce latte, extra hot with a dash of cinnamon, brought her a beautiful card in lovely old-style cursive to say she’d missed her and was so happy she was back. That’s a huge success.

We have an open kitchen, and when a customer walks up to the window, my kitchen staff gets nervous, thinking they’re about to get yelled at. But the customer just wants to say how much they loved their food, and my staff stands there like, “What do I do? Someone paid me a compliment!”

And a detailed review, where someone writes about how they felt there, is a real milestone for me.

I’d also love to pay the bills. That would be really nice too.

Which local businesses would you like to give a shoutout to?

Matthew: Since we’re a chamber of commerce, my final question: which other businesses would you like to highlight? Apart from each other’s, of course.

Tara: One of the newer businesses on Main Street: Comics Adventure. My older kids are comic book fanatics, in the best way, so we were longtime customers, and over time Bruce became a regular at the cafe. He told me about the challenges with his space, and I asked, “Have you thought about moving downtown?” I’m on the DOCA board, so I helped him work through his lease and find a space down here. It turned out he’d wanted to move downtown for years.

Now he’s doing great. The foot traffic is fantastic, and we’re helping each other’s businesses. When people visit multiple places downtown or in Midtown, that’s how small businesses succeed. Moving your location is a huge leap, and it was very brave of Bruce. He’s bringing families downtown, which we need more of. Fail fast, fail hard. Heck yeah!

Matthew: Go Bruce! Laurie?

Laurie: There are so many. In Midtown there’s the Hive, and on weekends I love the hardware store, which has music downstairs. It’s one of my favorite places to meet people after work. My hours are so different now that Sunday afternoon is my Friday!

Further down, I love Studio Gray, a little gift shop behind the comic book store. Dani is awesome. And on my way home, if there’s a spot outside Corcilla Cellars on a Wednesday, I’ll stop in. They have Wine Wednesdays with $5 glasses.

Thank you both so much for this conversation. We’re so grateful to have you, not only as Chamber members, but as fantastic businesses and people in our community. Oregon City is much better with you both here.