Lauren Sisak - Escapee 925 - entrepreneur success stories
Author: https://www.facebook.com/roblongley
Description: For almost a decade, Lauren Sisak did everything “right.” She went to business school at Wake Forest University
Date: 2026-01-19T19:06:13+00:00

# Lauren Sisak

Escapee | 0 |

> I approach life the same way I train dogs–embracing the chaos, rewarding the good, and keeping snacks handy for both of us.

For almost a decade, Lauren Sisak did everything “right.” She went to business school at Wake Forest University, and landed a stable job before her second semester of her senior year. She then spent 8 years knee deep in the sales world. It was a super male-dominated insurance and team, and she had to fight to be taken seriously. Her mentor, Neal Sweeney, was the kind of guy who wore a suit every day to a business casual office, complete with his tie chain, pinky ring, and L.A. Looks slicked back hair, reluctantly took her under his wing. “See, he wasn’t tech savvy, so I, as the millennial, made myself invaluable to him. I even made sure I never taught him how to do things so I was always useful.

For a while, chasing the commission checks really propelled me. Then I adopted Stella. She was supposed to be my well-behaved puppy after losing my senior dog, Sammy. He had bitten multiple people (myself included), but still came everywhere with me and was the goodest boy in his last years. I thought a puppy would be easier because I could “mold” her from the start. Spoiler: Stella had other plans. She was anxious, loud (and that means a lot since I am Cuban, born and raised in Miami), clingy, and hated being alone. She barked through my Zoom calls and refused to nap unless I was in the same room. I couldn’t go out, and nobody could come in, not even the super.

That isolation cracked something open in me.I hired a trainer for help and became obsessive about dog training. Just ask my best friends, I was probably insufferable. Before long, I was deep into training podcasts, courses, and Instagram rabbit holes. Out of curiosity (and maybe desperation), I started dog sitting on the side. I figured it would give me a break from Stella. It did, but every dog was just as anxious, reactive, or complicated. But instead of burning out, I lit up. I’d finally found something that felt meaningful, plus it made me appreciate Stella.

I know comparison is the thief of joy, but that is so hard not to do! Still, I wasn’t ready to walk away from the steady paycheck. I told myself I could balance both worlds: leggings and dog hair by night, blazers and spreadsheets by day. That lasted about a year — right up until the Sunday Scaries started lasting all week.So I did the unthinkable. I quit my very safe and cush 6 figure job to scale Sit. Stay. Stella. It terrified everyone around me, but I needed to know if I could do it.

Fast forward two years, and that leap turned into a thriving multi-six-figure business. There are20 Stellar Sitters, two admins, a social media manager, and Lauren. She always says that this isn’t less stressful, but it is her stress, and she would prefer that any day. Escaping the 9-to-5 didn’t happen overnight. It happened one brave, messy, dog-hair-covered step at a time.

## The Changing World

Lauren hadn’t started her business when Covid it, but it was pivotal for her getting started. She spent the time with her family in Miami, where she inherited her dog Sammy. He needed training, especially for walks, and it was Lauren’s first time training a dog. He ultimately flew back home to NYC with her, where he adapted to city life with a lot of patience and love.

AI is the current game-changer in the world today. Luckily, AI will never be able to dog sit. Lauren has seen certain companies use AI to give dog training advice. However, behavior modification for the dogs that need it most is quite complex. She cannot imagine a world where AI can accurately assess and develop a training plan.

To keep up with all the changes, Lauren listens to lots of podcasts. This includes: The Mel Robbins podcast, How I Built This , and On Purpose with Jay Shetty. She also made some lifestyle changes and gave up alcohol. “starting over can be deeply depressing, frustrating, and anxiety inducing, you need your head on straight! “

## Learning along the Way

“When I was in sales, the best ideas would need sooo many approvals. By the time it was approved, the idea was diluted, outdated, or shot down. Now, I can come up with an idea and execute it the same day depending on what it is. If protocol needs to change, i wave a magic wand, and it’s done. I answer tons myself at the end of the day.”

For Lauren, sobriety and therapy have been invaluable in her journey. A clear head and unbiased sounding board hits different than friends who, for better or worse, always want to build you up. “And on the subject of friends, know your circle will change. Who celebrates your successes may not be the same as who celebrated the old you. That is ok and means you are growing. Finances will be painful–I am still waiting for the less painful part, I will let you know how long it takes when I get there. “

If she were starting over, Lauren would have hired an admin from day 1. It is important to delegate any and every task you do not want to do that takes you away from being a CEO. She is still reaching for peak delegation, but every time she adds support to her team of 20 Stellar Sitters, 2 trainers, 2 admins, and a social media person, she never regrets it.

## The Tough Parts

Everyone makes mistakes in their journey. Lauren is not an exception. She said she probably already made 2 today. When she first started out there were a couple of instances of hiring the wrong people and expecting them to be something they were not. Resume’s don’t always tell us what we need to know. Lauren had some great insight on communication and expectations. “I find that when I am frustrated internally, it is because I have not communicated as well as I could have. My poor communication is usually because I am exhausted, overscheduled, and spread way too thin. “

She recently invested 7k in meta ads, which was an epic fail. “When I tell you we did not convert a single lead…it was horrible. It pained me that I could have spent that money on SO many other things. So the next month when I felt financial pressures, I was kicking myself because i HAD the funds at one point. They were there!!! But unfortunately, that is exactly what owning your own business feels like–shoulda, coulda, woulda. If you spend too much time in those moments, you will operate from a scarcity mindset and move at a glacial pace.”

## Moving On

Beyond scaling in Manhattan and Brooklyn, Lauren is developing a Stellar Sitter certification to replicate her unique model. The goal is to make as many sitters as skilled for reactive and anxious dogs as possible–helping the industry as a whole. All the time she is try to prioritize herself and triage her goals. “If I am able to execute on all of my dreams, I will have built something really special and impactful.”

Learn more about Lauren and her business at: sitstaystella.com

### About The Author

#### admin

Robert Longley is a coach, consultant, author of several books, world traveler and fixer of things. He helps mid-career professionals and entrepreneurs reignite their passion for doing work that matters. He currently is working on a project to rethink the way, and where, we do work.

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