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The First Autopilot for Self-Employment Finance
We are a smart bank account that
automates saving for self-
employment taxes & 1099 benefits
management.
The Freelance Economy
By 2020, 45% of US workers will be independent contractors.
55 millionAmericans are independent contractors today.
(They earn $1 trillion annually)
Stress Ignorance Savings
Over 40% of independent
contractors cite taxes as their
#2 issue (after finding work).
Over 40% of independent
contractors have no idea how much
they’ll owe in self-employment taxes.
70% of Americans can’t
cover a minor ($500 - $1000)
emergency.
! ? $
1099er Problems
$
$
$
$
$
$
$
$
$
$
$
$
$
$$
$$
$
$
$
$$
$$
$
$
$
Step 1
Income from multiple clients can be
deposited directly to Painless1099.
Step 2
Money for taxes is separated and held safe
in the user’s Painless1099 account.
Step 3
Spendable income (less taxes) is
sent directly to an account of the
user’s choosing.
How it Works
Direct to Consumer (B2C)
Marketing/content direct to
contractors about pains of
1099 taxes.
Current CAC < $100
Partnerships (B2B2C)
Notable Partners
First enterprise partner
Direct integration to Dream Town
Real Estate agent dashboard
Our partners say offering Painless1099 will
make hiring easier (it’s a value add) and
aid in retention (it’s a perk to drive loyalty).
Acquisition Channels
In a growing network of
content, channel, & small biz
CPA partnerships
Revenue Model
~$50 per referral
Partner
Referrals
Use income, cashflow, & credit data to refer
users to financial service & benefit partners
Contractor Perk
Have enterprises pay to have their
contractors to utilize Painless1099
Ideal depending on
the type of partner
Subscription
Charge users a flat monthly rate for benefits
facilitated through the Painless platform
Viable in the long
term w/ multiple benefits
Subscription
Charge users a percentage for usage meaning
they only pay when they earn
Interest Earn interest on assets held at Painless1099 Interest rate dependent
~$100 annually
per avg user
Qualified Leads in an Untapped Demo
Signup & usage allows us to collect income, cashflow, and
credit data to vet/qualify each user before selling a lead.
Mitigated Risk For Fraud & Credit
Rich data also helps monitor for fraud, while assets held for a user
can help set credit limits or collateralize access to new products.
Engagement
Critical high value touch points (earning, filing & reporting) through
lifetime provide ample opportunity to build trust and convert leads.
Why Will Partners Pay for Our Leads?
unemployment
insurance
healthcare
401k
The Future of Freelance Benefits
We designed the brand to extend beyond tax withholding as the core
offering. Our current technology easily connects with other platforms to
function as the very first “portable benefits package” for the 1099 world.
Projected customer lifespan of 5 years with subscription,
quarterly filing, and referrals equates to an LTV of $1,000.
Which makes Painless1099 attractive to a host of potential acquirers:
Platform Potential
Ace Callwood
Co-Founder & CEO
Justin Kauszler
Co-Founder & Head of Product
Co-founder, Coffitivity - TIME Top 50 Sites (2013)
Former Entrepreneur in Residence, Faculty at VCU
School of Business
Strategy, brand, & innovation consultant
Co-founder, Coffitivity - 3.5M+ Users
Former Lead, VCU Venture Group
Faculty technology commercialization expert,
VCU Innovation Gateway
Management
Brian Monbouquette,
CPA
Joe Kunkel Art Espey
Former Partner,
Price Waterhouse Cooper
(23 Years)
CPA

Fractional Startup CFO
Former SVP Marketing & Strategy,
CarMax
Marketing Expert
Executive Advisor,
New Richmond Ventures
Managing Director,
Paladin Global Services
Management Consultant &
Strategy Expert
Former Fortune 500 COO
Advisors
Saving/Withholding
Tax Calculation
Deposit to IRS
Automation
Competitive Watchlist
Total Accounts Opened
700+
Total Dollars Deposited
$2,500,000+
Average Account Balance
$2,400
Partner Bank
Lincoln Savings Bank
Startup Competition
43North
Runner up, 11,000 Applicants, $500K Prize
Powered by Techstars
Barclays Accelerator
Traction
Launch Date
April 2016
The First Autopilot for Self-Employment Finance
hello@painless1099.com
Appendix A: Prospective Referral Matrix
$
$
Invoicing
Retirement &
Unemployment
Business Banking
& Credit AccessHealthcare
Tax Prep
Income
Smoothing

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Painless1099 Deck

  • 1. The First Autopilot for Self-Employment Finance
  • 2. We are a smart bank account that automates saving for self- employment taxes & 1099 benefits management.
  • 3. The Freelance Economy By 2020, 45% of US workers will be independent contractors. 55 millionAmericans are independent contractors today. (They earn $1 trillion annually)
  • 4. Stress Ignorance Savings Over 40% of independent contractors cite taxes as their #2 issue (after finding work). Over 40% of independent contractors have no idea how much they’ll owe in self-employment taxes. 70% of Americans can’t cover a minor ($500 - $1000) emergency. ! ? $ 1099er Problems
  • 5. $ $ $ $ $ $ $ $ $ $ $ $ $ $$ $$ $ $ $ $$ $$ $ $ $ Step 1 Income from multiple clients can be deposited directly to Painless1099. Step 2 Money for taxes is separated and held safe in the user’s Painless1099 account. Step 3 Spendable income (less taxes) is sent directly to an account of the user’s choosing. How it Works
  • 6. Direct to Consumer (B2C) Marketing/content direct to contractors about pains of 1099 taxes. Current CAC < $100 Partnerships (B2B2C) Notable Partners First enterprise partner Direct integration to Dream Town Real Estate agent dashboard Our partners say offering Painless1099 will make hiring easier (it’s a value add) and aid in retention (it’s a perk to drive loyalty). Acquisition Channels In a growing network of content, channel, & small biz CPA partnerships
  • 7. Revenue Model ~$50 per referral Partner Referrals Use income, cashflow, & credit data to refer users to financial service & benefit partners Contractor Perk Have enterprises pay to have their contractors to utilize Painless1099 Ideal depending on the type of partner Subscription Charge users a flat monthly rate for benefits facilitated through the Painless platform Viable in the long term w/ multiple benefits Subscription Charge users a percentage for usage meaning they only pay when they earn Interest Earn interest on assets held at Painless1099 Interest rate dependent ~$100 annually per avg user
  • 8. Qualified Leads in an Untapped Demo Signup & usage allows us to collect income, cashflow, and credit data to vet/qualify each user before selling a lead. Mitigated Risk For Fraud & Credit Rich data also helps monitor for fraud, while assets held for a user can help set credit limits or collateralize access to new products. Engagement Critical high value touch points (earning, filing & reporting) through lifetime provide ample opportunity to build trust and convert leads. Why Will Partners Pay for Our Leads?
  • 9. unemployment insurance healthcare 401k The Future of Freelance Benefits We designed the brand to extend beyond tax withholding as the core offering. Our current technology easily connects with other platforms to function as the very first “portable benefits package” for the 1099 world.
  • 10. Projected customer lifespan of 5 years with subscription, quarterly filing, and referrals equates to an LTV of $1,000. Which makes Painless1099 attractive to a host of potential acquirers: Platform Potential
  • 11. Ace Callwood Co-Founder & CEO Justin Kauszler Co-Founder & Head of Product Co-founder, Coffitivity - TIME Top 50 Sites (2013) Former Entrepreneur in Residence, Faculty at VCU School of Business Strategy, brand, & innovation consultant Co-founder, Coffitivity - 3.5M+ Users Former Lead, VCU Venture Group Faculty technology commercialization expert, VCU Innovation Gateway Management
  • 12. Brian Monbouquette, CPA Joe Kunkel Art Espey Former Partner, Price Waterhouse Cooper (23 Years) CPA
 Fractional Startup CFO Former SVP Marketing & Strategy, CarMax Marketing Expert Executive Advisor, New Richmond Ventures Managing Director, Paladin Global Services Management Consultant & Strategy Expert Former Fortune 500 COO Advisors
  • 13. Saving/Withholding Tax Calculation Deposit to IRS Automation Competitive Watchlist
  • 14. Total Accounts Opened 700+ Total Dollars Deposited $2,500,000+ Average Account Balance $2,400 Partner Bank Lincoln Savings Bank Startup Competition 43North Runner up, 11,000 Applicants, $500K Prize Powered by Techstars Barclays Accelerator Traction Launch Date April 2016
  • 15. The First Autopilot for Self-Employment Finance hello@painless1099.com
  • 16. Appendix A: Prospective Referral Matrix $ $ Invoicing Retirement & Unemployment Business Banking & Credit AccessHealthcare Tax Prep Income Smoothing