I'M
JOSH
CHERNIKOFF

ENTREPRENEUR & BUSINESS COACH
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I’m Josh, an entrepreneur, and small business advisor. For the last 14 years, I have founded and grown two successful educational enrichment programs serving hundreds of thousands of students in 85 schools across six states. These businesses have achieved triple-digit growth, received noteworthy press, and feature innovative, best-in-class technologies. Thus, as an entrepreneur and small business advisor, I’ve worn about every hat imaginable. That means if you’re experiencing a pain point in your business, I’ve probably come across the same thing too. So whatever your goals are, I’m here to help.

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WHAT MY EXPERIENCE IN THE EDUCATION SPACE CAN DO FOR YOU

SMALL BUSINESS ADVISING

ENTREPRENEURSHIP COACHING

THOUGHT LEADERSHIP

STRATEGIC PLANNING

 
 

PORTFOLIO

MY LATEST WORK
 
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EXPERIENCE

2022 - Present

CASCADE COMMUNICATIONS

Founder/CEO

2021-Present

PODCASTING

Lead Podcast Host

Coach small businesses and startups in the education space, providing strategic advisement and ongoing mentorship.

Position C-suite entrepreneurs as industry thought leaders via market development and content creation.

How I Broke That: For better or worse, most business owners have “broken” themselves, their business, or their industry at some point. Josh Chernikoff, a serial entrepreneur who has successfully grown (and broken) three bootstrapped businesses, interviews other entrepreneurs to learn how they built, broke, and rebuilt within their industry. Each episode will simultaneously induce cringes and provide comfort in helping you realize you are not alone in breaking something on your path to innovation.

Mobilize 6-person global cross-functional team in automation, lead generation, email deliverability, and content development to engage and nurture leads.

Build sales pipeline for clients utilizing HubSpot and Pipedrive, generating 100,000+ leads to facilitate successful partnerships.

Provide consulting for 15+ clients: A&A Creative Happenings, BLOQQ, Clickto, DataNuts, FirstRoot, Flex, Flex Tutors, Jumpstop Academy, Little Hoopers, Overtime Athletics, Paytheory, Possble.ME, SurfWisely, Wellness Travel Association, and WellUp.

2021 - Present

FLEX TUTORS

Founder

Breaking the Grade: a thought-provoking podcast that follows entrepreneurs as they transform learning and advance equity and impact in the global education space. Tune in for stories about breaking norms, introducing new ideas, and shaping our future through every lesson learned.

Lifelong Educators Show: COVID and technology has changed what we thought was possible in education, but what does this mean for educators? The Lifelong Educators Show, presented by Clickto, was designed to answer this exact question. We will showcase and learn from our community of educators that are successfully adapting their businesses to not just service, but to increase the impact they can make in their students’ lives. At Clickto, we believe that the future of education is community, accountability, and interactivity.

Launched an online tutoring platform under the Flex Academies brand to combat learning loss and deliver educational enrichment in the K-12 space.

Implemented an innovative tutor-matching system, pairing students with top quality tutors based on learning needs and personality fit.

2018 - Present

BOARD SERVICE / LEADERSHIP

Board Member

Mobilize individual/group tutoring to help students achieve educational growth at pre-pandemic levels.

Facilitate scholarship access for families experiencing financial hardship, granting all scholarship requests from day one.

Jumpstop Academy: a basketball academy designed to help kids foster their enjoyment of the game while growing life skills.

Stronger Brains: a program providing schools with affordable, accessible means to assess/document students’ brain health and increase academic performance and personal wellness.

WellUp: an educational health platform connecting student information with schools to share information through a centralized portal.

Milken-Penn GSE Education Business Plan Competition Volunteer Judge

2011 - Present

FLEX ACADEMIES

Founder

Founded and grew educational enrichment platform to 85 schools in 6 states.

Constructed high-performing teams while rolling out new CRM and technology implementations including Zoho and Salesforce.

2007 - 2018

ASHLEY TUTORS

Founder

Innovated a human-powered matching system to connect tutors with 1,200+ students and families across the D.C. region.

Built a team of 65+ highly educated tutors with degrees from Top 100 universities.

Introduced new technologies and fostered a data-driven environment to capture student success rates.

Achieved feature stories on NBC4 News and WUSA9 News.

Achieved 96% or higher client retention rates and 104% three-year growth in student population.

Featured on behalf of Flex in numerous stories and interviews on local NBC, ABC, and CBS affiliates.

Successfully sold and transitioned company operations in May 2021.

2003 - 2007

PROFESSIONAL BROADCASTING

Sports Anchor, Editor, Writer, and Producer

Anchored 2 sports news broadcasts for the Washington Football Team Broadcast Network from 2006-2007.

Attained over 3 million online views per year.

Served as Lead Weekend Sports Anchor at WHSV-TV from 2003-2004.

Covered DC-area high schools, colleges, and professional teams, reporting nightly sports news and highlights.

TEAMS WE ARE CURRENTLY ADVISING

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pay theory
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TESTIMONIALS

Josh gets what makes learning fun for kids, and he has the business acumen to take it to scale.

As a superintendent, he is what I look for in a provider to help increase opportunities for students. He has a big vision and the attention to detail needed to be a great partner: kid-centered and operationally excellent.

Brian Osborne

Former Superintendent

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CONTACT

Please feel free to share your contact information with me and a brief message describing the challenge you’re facing and what you hope to gain from my services.

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