"I had no idea what I was going to do. I just knew it wasn't that."

Two former corporate full-timers walked away from the ladder they'd spent a decade climbing and built a business and a whole new set of rules. 

We recently sat down with Katie Toscano & Ashley Maripol of Cabot & Main and The Rewrite Project to discuss the fears and freedoms that come with building your own business. 

Meet the Founders

Cheyenne: Today we're here with Katie Toscano and Ashley Maripol, co-founders of Cabot & Main and The Rewrite Project. We're talking all things going from corporate professionals to badass business ladies. So I'll hand it over to them to introduce themselves!

Katie: I'm Katie Toscano, co-founder of Cabot & Main alongside my business partner Ashley. We founded it about five or six years ago, and we also just kicked off The Rewrite Project earlier this year. We're former corporate accountants and operations girlies. Cabot & Main focuses on operations for accounting firms. We make sure things are done the right way through automation and systemizing. We're both moms, dog owners and live in Orange County.

Ashley: I'm Ashley. Katie and I used to work together in corporate and had the opportunity to leave and start our own thing together. It's kind of a unique journey, but we're excited to talk about it.

The Breaking Point

Cheyenne: What were you doing before Cabot & Main, and what was the moment you decided you'd had enough?

Ashley: For me, there wasn't one big moment but rather a lot of little ones. I started at the firm straight out of college and worked my way up. I'm grateful for my time there but I quickly realized autonomy is so important to me. I want a say in what I do and how I pursue it, along with flexibility. I remember interviewing at another firm when I was unhappy and thinking, "The grass isn't greener. I'm jumping from one thing to the exact same thing somewhere else." So that was probably when I started asking, "What could I do if I worked for myself?"

Katie: Mine was different. Around year ten I'd gone part-time thinking it would solve my problems. It did not. My husband was living in downtown LA for a work program for four months, so I was home with two little kids, working "part-time" that was really full-time, traveling, doing every single thing a working mom does. I thought I was going to lose my mind. As soon as he was back, I said, "I can't. It's time." I had no idea what I'd do. I just knew it wasn't that.

"I feel like the grass is not greener over there. I think I'm jumping from one thing to the exact same thing somewhere else." — Ashley

 

Cheyenne: When you started your careers, what did 15, 20 years out look like? Did you always think you'd start a business?

Ashley: I definitely thought I'd retire from corporate life. I'm so risk-averse. When I told my mom I was leaving, she said, "You worked so hard for this! What are you doing?" Owning a business never crossed my mind early on. It wasn't on my bingo card.

Katie: Literally never. I thought that was for outgoing people, risk-takers—everything I am not. The only reason I ever considered it is because of Ashley. We were standing outside our cubicles and she told me about the online business world and this coach she'd found, and I thought, "Wait. ould I do that?" It didn't sound impossible anymore. I got the bug and about a month later I was in.

The Leap (and How Long It Took)

Lauren: Every business owner started at step one. Katie, I want to be you — you had the idea and did it a month later! Ashley, from your first idea to your first step, how much time passed?

Ashley: I'm a marinate-on-it person. Mine was a slower journey. The coach I found came from a really good online ad that just spoke to me. I thought, "How does she know me?" That got me into the idea that I could do things I'm good at online and serve other businesses. But I had to think hard about the finances; we relied on my corporate income and bonuses. So I started slowly by setting things up and got a couple clients to try it out. So from the day I had the idea to leave until the day I actually left was probably about a year.

Jennifer: What's the thing about entrepreneurship that surprised you the most?

Katie: Everything! The autonomy was a surprise. In corporate your 8-to-5 is laid out. There are spoken and unspoken rules about how you report, how you talk to people, how you spend your time. It's very detailed. Then you start your business and you totally own your time, which is great, but there's no accountability except to yourself. I hated that corporate structure, so for me that was freeing. The other thing is the inconsistency. You aren't gifted a salary, you have to work your butt off to find every single client, and it's really hard. Then you fail, try again, it works, then it fails again.

"You fail so often and so publicly that it's like, 'Okay, yep, we did that again, now we're moving on.'" — Katie

Ashley: I thought I'd leave and suddenly have all this flexibility and feel less stressed. What took me a while to realize is that I had certain rules in my head about how I should work. I have a hard time saying no. If you keep operating by the same rules you had in corporate, you can put yourself right back in that same place without meaning to. We'd grown really quickly, and there was a point I said, "Why did I even leave? This is insane." So take a look at how you want to operate now that you have the freedom to.

On Failing Publicly

Jennifer: Katie, your thing on failure is speaking to me. It reminds me of that Keke Palmer interview where she said she's the queen of reframe — "It's not that I didn't get the job, it's that you didn't get the pleasure of hiring me." Sometimes you have to be delusional enough to say, "It's fine. It's fine!"

Cheyenne: Any tips for getting over failing publicly? Or is it just doing it repeatedly until you're over it?

Ashley: It's a bit of doing it repeatedly. If we don't, we hold ourselves back from so many good things. Failure's part of it, and it's gotten more comfortable the longer we've done this.

Katie: We're five, six years in and I've got about eight years of public failure experience at this point, and it's gotten a lot easier. The nice thing is you'll very quickly move on and fail at something else, so the attention keeps moving! Practically speaking, you can block people on your socials if you don't want them to see it. But most of our early growth came from people we knew and their referrals. And people really relate to it. When someone connects to a failure you shared, it lifts your heart a little.

Ashley: Being perfect isn't relatable, because none of us are perfect. I don't want to see a business that's polished and perfect all the time. Seeing real humans makes me think, "I want to be part of that."

"Just block everybody you know! If that's the thing that's stopping you — block your husband if you need to. Just do the thing." — Jennifer

 

The Money Question

Cheyenne: For the three of us at MiMo, we're actually the primary breadwinners in our households, so moving into entrepreneurship without steady income was very scary. Ashley, as the numbers girl... what did that look like for your family? What was the path where you said, "This is when I'll take the leap"?

Ashley: I looked at our budget and what our spending typically looks like, and plugged in my husband's salary. Then looked at what's the bare minimum I need just to keep afloat? Not what I want to make, but if I cut back, what could that look like? Once I had that number, I backed into it: what are my services, how much do I charge, how many clients does that mean I need? Working backwards gave me a sense of control. We still look at cash flow month by month: what's recurring, where new projects fall, and that takes away a lot of the anxiety around the uncertainty.

Katie: Ashley's a spreadsheet girl. She keeps us aware because I'm honestly bad at that. One thing a coach walked us through was worst-case-scenario planning. "If this happens, then what? And if that happens?" then repeated it to the absolute worst case scenario. It's not fun, but going through it deliberately helps you realize that the worst case is you go back and get a job, or get a couple new clients. Having that in your back pocket is a good mindset exercise.

Lauren: My mind always jumps to, "I'm one step away from losing everything." But there are a million steps between now and then. Putting pen to paper reminds me I'd have to make a lot of mistakes for that to happen and I won't let it.

Jennifer: We also take for granted the support systems around us. There are so many grants for women going into entrepreneurship, client boards, little things you can do. My husband went full worst-case, "We're going to live out of a box!" and I said, "Our actual worst case is we move in with our parents. Nobody's letting their grandbabies live in a box." Going to the extreme actually became a weird pick-me-up.

Did It Actually Deliver the Freedom?

Cheyenne: You wanted autonomy, your time back, flexibility. Did entrepreneurship actually provide that?

Katie: Yes! It's a game-changer. It's not perfect and there are still client meetings and deliverables but the freedom is unreal. I'll go for a walk and coffee on a Wednesday and it's the best thing in the world. When you don't have a boss over your shoulder, it'd be really hard to go back.

Ashley: The autonomy came quicker for me. Flexibility took longer, because I kept those same rules on myself. Katie was great at setting boundaries around her time (when we're available to clients and when we're not) and I learned a lot from that. "Oh, it's okay if I do these things. Our clients are still here, and they're still happy."

Wellness and Boundaries

Lauren: How did wellness shift when you went from working for someone else to working for yourself? When I had structure, self-care fit around it. Now, without someone else's expectations, my wellness has slid to the sidelines.

Ashley: A business coach told Katie and me, "You're looking at this wrong. That's your number one focus, and you fit everything around that." That shifted things for me. I have a slower morning now where I'm able to get my kids to school and take a moment for myself. And I show up to work so much better. I'm not available as early as I used to force myself to be.

Katie: That's the autonomy piece: you get to choose it, Lauren. Block your calendar. Put whatever wellness means to you on there, and then don't be available for meetings at that time. For me it's Tuesday, Thursday, Friday mornings. They're non-negotiable, blocked. Not available for clients, not even for Ashley unless it's urgent. Blocking my calendar was the number one thing that helped.

Starting a Business With a Friend

Cheyenne: Everyone says, "Don't start a business with your friend!" How did you two make it work?

Ashley: I'm an Enneagram 9 so my core need is safety, harmony, peace, so I don't like conflict. But conflict is essential to growth. Katie and I have different working styles, and over time those have come into conflict. My advice: have the conversations. Approach them with love and support. Every time we do it it feels uncomfy in the moment but we end up in such a great place. It's honestly been a safe space to practice better conflict skills for the rest of my life. Don't shy away from the conflict.

Katie: Ashley being a peacekeeper has saved us a lot. What I didn't expect is that at the beginning it literally felt like a marriage where we're making big decisions together with someone you're not related to, genuinely caring how the other person feels because you need it to work. Hot tip: we use Voxer, voice notes. There's no question about tone, you can word vomit, and you don't have to respond right away. If we hear something uncomfortable, we sit with it and come back after we've actually thought about it. That tool is one of the most useful things we've done for managing conflict.

"It literally felt like a marriage where we're making really big decisions together with someone you're not related to." — Katie

 

Jennifer: I want to put Lauren in the hot seat! Lauren's the connecting person between Cheyenne and me. Same question for Lauren... how do you manage friendship in this group dynamic?

Lauren: I just hang up on you guys! Kidding. There are three of us and I'm the middle one. I met Cheyenne at one job and Jen at another. It's like a marriage, but a throuple. Getting to know you both in a workspace that's different from a personal space has helped me grow. Even practically, like how you like to receive information. I have a hard time editing back, so my updates run eight pages long, and I know it drives you both crazy. Last week Cheyenne added extra info to a message just for me, and it made me feel seen. The three of us mesh because we're human-first, never business-first. It's always friendship and life first, then business. I grew up a people pleaser afraid of conflict, because I thought conflict meant we wouldn't be friends forever. I've learned it's okay. Conflict is healthy, you talk through it and come out stronger.

Jennifer: Kudos to Lauren, who won't say this about herself but she came into MiMo saying, "Whether it's one person or everyone on the call today, we're doing a culture activity!" That's been huge for self-awareness, which helps conflict resolution and brought Cheyenne and me closer. Shout out to Lauren.

One Piece of Advice

Cheyenne: If you could give one piece of advice to someone in corporate right now who's afraid to take the leap what would you say?

Ashley: Look at why you want to go on this journey. Identify that why and your values up front, and build around it. We talked a lot about boundary-setting. In corporate we're used to "yes, we can do that," overextending ourselves. Be true to your why on your own. You can make almost anything work, so it's more about how you'll do it, not whether you can.

Katie: I agree. Figure out what you want it to be. But also decide honestly whether it's right for you, because it isn't for everybody. If it fits your life and you want it, do absolutely everything to make it happen and move past every roadblock. But if you're unsure, take your time. You have to be able to live with the uncertainty and the risk. And do the internal work on your self-limiting beliefs. Get to know yourself really well-your strengths, your Enneagram, what you're actually good at-and treat those as your biggest value because they're your gifts. That little voice will tell you you're not good enough constantly. Shove it aside and keep going.

Cheyenne: I'll add one for you both, because you dropped nuggets through this whole conversation about rewriting the rules aka what society tells you to be and how to act. Which is the perfect segue into your new project!

The Rewrite Project

Ashley: With The Rewrite Project, Katie and I reached a point where we realized there are certain rules we're either born with or learn from society, like "I have to keep climbing this corporate ladder." As two highly ambitious women, sometimes we don't know what else there is. So it's about looking at those rules and rewriting them to live a life full of joy. We're still leaning into our ambition, but maybe that looks a little different.

Cheyenne: A lot of people don't notice they're living by rules society gave them until it's said out loud. That's needed.

Where to Find Katie & Ashley

Find Cabot & Main on Instagram @cabotandmain and at cabotandmain.com. Their brand-new Substack is @therewriteletters, where they share monthly on rewriting the rules for themselves and hopefully for you too.

Catch more conversations like this on The Momentum Sessions — YouTube, Spotify, and @themomentumsessions on Instagram.