ITV #271: She Went From Making $10K a Day to Building a Seven-Figure Tax Business | Inside The Vault

Cheyenne Drayton’s story is bigger than taxes. Before becoming a multi-seven-figure business owner, Cheyenne says she was making roughly $10,000 a day in the streets .

But behind the money was survival mode, instability, and a life that almost cost her everything. After being robbed, raided, spending five days in jail, and losing custody of her children, Cheyenne made a decision: there was no Plan B.

She went all in on the tax industry. In her first year, Cheyenne says she built a team of more than 300 tax professionals and generated approximately $464,000 .

Pasted text Inside the Vault, Cheyenne opens up to Ash Cash about growing up homeless, becoming a teenage mother, rebuilding her life after the streets, learning how to manage money, creating income beyond tax season, and using AI and automation to build a business that gives her more time with her three sons. She also shares why her greatest wins aren’t always the million-dollar results — sometimes it’s watching someone on her team go from sleeping in a car to finally being able to support themselves.

In this episode: • Making $10K a day in the streets • The robbery that made her question everything • Getting raided, going to jail, and losing her children • Making $464K her first year in taxes • Scaling to 300+ tax professionals • Creating income outside of tax season • Monthly recurring revenue and digital products • Using AI to answer client and team questions 24/7 • Automating a business so you can get your time back • Motherhood, faith, and raising three boys • Supporting her son through Duchenne muscular dystrophy • Why your past does not have to determine your future • Learning to love yourself instead of searching for it in others Cheyenne’s message is simple: sometimes nobody is coming to save you — and your future does not have to look like what you’ve been through. Pasted text Connect with Cheyenne Drayton: Instagram / TikTok / YouTube: @thecdrayton Website: Free Tax Industry Masterclass: Every Tuesday Inside the Vault: @insidethevault Host: @iamashcash ABUNDANCE IS YOUR BIRTHRIGHT.

Join Ash Cash and a community focused on building wealth, increasing income, strengthening your mindset, and creating a more abundant life: TIMESTAMPS 00:00 – Cheyenne’s story in her own words 01:02 – Ash Cash book CTA 02:03 – Welcome to Inside the Vault 04:48 – Meet Cheyenne Drayton 05:50 – Becoming a multi-seven-figure entrepreneur 06:30 – Growing up homeless and in survival mode 07:28 – Getting into the streets 08:15 – 300 tax professionals & $464K her first year 10:36 – Making $10K a day in the streets 11:10 – The robbery that changed everything 12:06 – Her son’s diagnosis and reconnecting with God 12:40 – The raid she saw as an answered prayer 12:56 – “God, give me one more chance” 13:50 – How she found the tax industry 15:52 – Five days in jail to tax season 17:05 – Learning how to manage legitimate money 19:42 – Why she pours into other women 25:35 – From the streets to multimillionaire 26:46 – Making money beyond tax season 27:28 – Monthly recurring revenue & digital products 29:54 – The wins that matter most to Cheyenne 33:12 – Why she recommends the tax industry 35:35 – How Cheyenne uses AI in her business 36:40 – Automating a team of 300+ tax professionals 38:26 – Buying back time as a mother 40:05 – Her son’s battle with Duchenne muscular dystrophy 45:17 – Your future doesn’t have to look like your past 47:09 – What she would tell her 18-year-old self 48:19 – Cheyenne’s free tax masterclass 49:12 – Next Level Wealth 51:20 – Connect with Cheyenne 51:30 – Closing the Vault Advertising Inquiries: Privacy & Opt-Out: