25 Years Of Home Service ExperienceGet To Know
Caleb Wininger

Small Business Coach | 7-Figure Home Service Business Owner | Published Author | World Class Coffee Drinker | Husband | Father | Accomplished Public Speaker | Almost Made It On Jeopardy! | Begrudging Cat Owner

Caleb Wininger started his first home services business in 1999.  Over the years, he has developed a talent for identifying and solving problems in business through the use of systems.  A deep and careful thinker, Caleb has a unique talent for bringing new perspectives to any project or organization.

In recent years, Caleb has developed a passion for supporting other small home service business owners, with the goal of helping them achieve their entrepreneurial and life goals.  Serving as a certified CONQUER coach has given him new opportunities to connect with and impact owners at a high level.

CONQUER Certified Coach
Behavioral Essentials Certified Coach
Goldman Sachs 10,000 Small Businesses Alumn
Serial Entrepreneur
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November 1999

Lake State Cleaning Founded

In the fall of 1999, with no resources, no contacts, and no plan, Caleb started a window cleaning company in the metro-Detroit area.

June 2003

The Leader In The Market

Quickly, LSC gained momentum.  Caleb successfully carved out a niche in the luxury estate demographic.  Lake State Cleaning became the go-to exterior cleaning provider for many of Michigan’s most prominent residents.


October 2005

The LSC Team Grows

After several years of wearing the owner/operator hat, Caleb recognized the need to build a strong team.  He threw himself into learning everything he could about business management, entrepreneurship, and team development.  As a result, Lake State Cleaning’s growth accelerated.

August 2011

New Services, New Direction

In the mid-2000’s, Lake State Cleaning added additional services to its suite of offerings.  Power washing and soft washing were natural add-ons to window and gutter cleaning.  This shift in focus would ultimately take LSC to new heights in terms of revenue, market share, and overall direction.


July 2015

Hidden Talents Revealed

In the summer of 2015, Caleb built a quite impressive rock cairn on the shores of Lake Michigan.  This really has nothing to do with anything, I just think it’s cool.

July 2015

More Accolades

Lake State Cleaning was awarded Best Of 2015 in the exterior cleaning category in our market… basically without even trying.  They sent us this nice sheet of (wrinkled and creased) paper to let us know.

July 2019

Goldman Sachs 10,000 Small Businesses Graduate

In 2019, Caleb was accepted into the coveted Goldman Sachs 10kSB program, held at Wayne State University in Detroit, MI.  During this 4-month “mini-MBA” crash course, Caleb made deep personal and professional connections and was nominated by his peers to serve as Cohort Ambassador.


January 2020

CONQUER Summit 2020

Award Winner & Speaker

The 2019 CONQUER Summit was held in Lake Tahoe, CA.  Caleb spoke to an audience of over 250 home service pros on the topic of perspective.  He was also privileged to receive several awards, including the first-ever Golden Carabiner award.  The winner of this annual award is recognized as the year’s top contributor to the CONQUER community.

February 2020

Responsicon 2020

Featured Speaker & Hacking Workshop Host

Caleb was a featured speaker at Responsicon 2019.  He spoke on the topic of memorable customer experiences.  He also hosted a hacking workshop on building compelling proposals.  This event, with over 300 contractors in attendance, is the home service industry’s premier sales conference.  Caleb’s company, Lake State Cleaning, also won the “GOAT Award” for being the company with the most quotes sent through Responsibid.

August 2020

More Growth For LSC

By the summer of 2020, Lake State Cleaning had grown to surpass $1,000,000 in revenue, with over 20 team members.  Despite the ups and downs caused by the COVID-19 pandemic, the team was stronger than ever.  Caleb handed over day-to-day operations to a strong management team and began to explore new professional interests.

January 2021

Podcast Guest Speaker

Caleb has enjoyed the privilege of joining some of the leading home services podcasts as a special guest and subject matter expert.  The Nicejob Podcast, Fight Club 4 Business, and The Jill’s Office Podcast are a few of his favorites.

December 2020

CONQUER Certified Coach

At the end of 2020, Caleb achieved is goal of becoming a Certified CONQUER Coach.  CONQUER is the world’s leading coaching and mentorship organization that is exclusively focused on small home service businesses.  After participating in the program as a client for several years, Caleb was thrilled to transition into a coaching role.

January 2022

The 2022 CONQUER Summit

Workshop Facilitator, Panel Speaker & Award Winner

At the 2022 CONQUER Summit, Caleb served as a workshop coach, working closely with a number of home service pros from around the country.  He also joined the coach’s panel, where he participated in a Q&A session with an audience of over 300 home service business owners.  The event was capped off for Caleb when we won “The Q Award”, the only one of it’s kind, as recognition for his unique contributions to the CONQUER program and community.

August 2022

The 2022 Huge Convention

Guest Speaker & CONQUER Booth Host

At the 2022 Huge Convention, Caleb was privileged to speak to an audience of over 100 pros on the topic of effective systems creation.  He also enjoyed hosting the CONQUER booth at the trade show, where he was able to connect with numerous home service business owners.

October 2022

Behavioral Essentials Certified Coach

In the Fall of 2022, Caleb was thrilled to earn a Coaching Certification from Behavioral Essentials, the world’s most respected behavioral assessment and modification organization.  Caleb is excited to continue learning more about this field and how it can be used to help home service business owners level up their teams.