All about the freelancers

“We are like hunters and gatherers” – Pam Liou


Last week we received a lot of good feedback, particularly on what group of users we should focus on first. It came down to freelancers. There are a lot of opportunities in this market because of various reasons:

  • lack of financial management tools that support specific needs of freelancers (personal + business accounts and multiple companies/clients/projects)
  • lack of standards on rates and best practices
  • growing market (more recent graduates are doing independent work)
  • I have understanding of everyday challenges of freelancers (freelance experience, and hiring freelancers/contract workers)

These opportunities also present challenges, namely the fragmentation of the market and lack of consistent documentation/census (not to mention international workers). Luckily, there is the Freelancers Union, which provides data on their members and have a lot of useful content in one centralized place.

53MM freelancers in the US

Based on a 2014 survey commissioned by FU and Elance-oDesk there were 53MM freelancers in the US.

“Gone are the days of the traditional 9-to-5. We’re entering a new era of work — project-based, independent, exciting, potentially risky, and rich with opportunities.”

“There are more avenues available to find work, to make contacts, to connect with others, etc. thanks to technology and its ability to network.”

  • 40% independent contractors: don’t have employer, work on a project by project basis
  • 27% moonlighters: have employer, moonlight on the side
  • 18% diversified workers: combination of different work types (full time secretary + uber driving + freelance writing project)
  • 10% temporary workers: single employer/client that is temporary (1-2 months)
  • 5% freelance business owners: 1-5 employees, also considers freelancers

Here’s a great tree of the interview questions they used to categorize the workers.

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FU also provides a report on their members. Here are some useful summaries from the post.

Key takeaways

  • For Millennials, freelancing is the new normal.
  • Concentration in the following fields
    • artists & creatives (38%)
    • services & sales (25%) — Lawyers, nannies, accountants, chefs, yoga instructors (kind of all over the place)
    • writers & editors
    • tech & web dev
  • Cities: New York still has the majority of FU membership (over 60%), other cities are (from highest growth to lowest)
    • LA, SF, Portland, Detroit, Baltimore, Milwaukee, Kansas City, Denver, Austin


Biggest challenges for freelancers: nonpayments and late payments

  • “One in every two freelancers had trouble collecting payment in 2014”
  • The average unpaid freelance worker loses almost $6000 annually – which accounts for 13% of their total income

It would be helpful to have a Glassdoor for freelancers with features such as report nonpaying companies and ratings, and help with written contracts.

There needs a way for freelancers to assess the risk of not getting paid by a company, and weigh the importance of experience/portfolio showcase piece vs. financial earning.   

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Frequent offenders:

  • 43% of respondents had trouble collecting payment from microbusinesses (1-5 employees)
  • 40% had trouble collecting payment from small businesses (5-49 employees)
  • 36% had trouble collecting payment from medium (50-149 employees) and large (150+ employees) businesses

Most freelance engagements aren’t protected by clear, written contracts.

  • Only about one-quarter of freelancers (28%) say they always use a contract
  • 33% say they always put the terms of agreement in an email
  • 42% always use a verbal agreement
  • 21% of freelancers have worked with clients who have refused to sign a contract

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Learning from the pro

Interview with Michael Gawley, Partner at Eisneramper.
  • list where usually spend money
    • schedule it out based on necessity or padding
  • create budget
    • look at historical (6 months – 1 year)
    • understand how to spend in the future
    • find impulse buys
  • what to cut (how to cut)
student transition (reliant on parents -> independent)
  • happens when get a job (easier for parents to cut cord)
  • period of adjustment: when gets paid, when need to pay (rent)
  • need tough love
    • parents cut credit cards
fiscal management: 3 groups
  • don’t care, can’t change
  • income and spending close: can be helped
  • already disciplined in financial management
for tough group
  • need credit counseling
    • figure out how spend money (lifestyle)
  • impulse purchases
  • only use cash ($40 for week, no more, one credit card for emergency)
  • debt relief
    • fuck up credit score, ruin a lot of things in life (rent big items, buy anything, loans)
  • no penalty until card declined
  • lack of financial discipline
    • behavior issues
learning financial management
  • have a spreadsheet
    • 52 weeks
    • when money comes in
    • list out expenses in order of most important
    • find what is not needed (optional spending)
    • decide level of discipline
how to save
  • budget: look at historical
    • find patterns: spend more in summer, fitness lifestyle
  • find where impulse spend
  • identify and analysis (from recent credit card data)
    • do you really need this
    • highlight issues
    • do you need a second job
  • need an “adult” who is responsible
  • if mess up, no second chance (from investors, banks, etc)
  • investors (analogous to parents in this situation)
freelancer issues
  • getting paid
    • try to avoid assuming risk of client (paid when get paid problem)
  • get money upfront
  • stop work if don’t pay on time
  • choosing clients
    • what is the chance of not getting paid
      • reference from other freelancers
      • check on business bureau for complaints
      • credit search (Standard and Poor)
  • separate business from personal
    • if audited: won’t open up everything in personal accounts
multiple partners
  • create legal entity: everything should go through business
  • all liable is something goes wrong
  • who binds the partnership
    • who is the adult?
Financial advisors perspective
  • (software) model spending habits (from last 12 months – 2 yrs)
  • help to understand where money is coming in and going out
  • best to talk to FA before college
    • college is first time can spend freely
    • learn to be responsible
  • provide independent advise outside family structure (not mom and data)
    • different scenarios in non-confrontational way
  • build trust
    • need to have respect and confidence in the person
    • need to get along with the person
    • comfort zone and immediate rapport
    • empathy
    • connect (same generation and language)
  • help to understand what to do if things go wrong (protect)
  • most tedious
    • paperwork
    • value in work: seeing as commodity
      • gatekeepers to regulatory side
      • not incentivized to provide improve experience (when viewed as commodity)
    • getting paid (20% of customers
Existing wealth management
  • family net worth 2MM+
  • FA start engaging around 11-12 yrs
    • incentivized so will stay with firm
  • provide webinars or workshops with other kids to talk wealth
  • estate planning
Financial ed
  • would be great to have in high school
  • 8-10 hrs a semester
  • different concepts
    • emotional vs practical
    • different types of people: what type is this?
  • department of ed: build pilot program in a school district
advice for us
  • use existing models (decision trees)
  • use other software to plug and play
    • negotiate license fee (by user #)
  • coaching side is more important
  • like weight watchers (call up coaching)
    • “you are better person for this”
  • partner with counseling center
    • pro bono credit crisis counseling: charity and church
    • paid services (bankruptcy crisis): need to pay upfront

Learning financial managment


  • self-employed status impacts tax situation
  • what kind of return: LLC, individual (1040)
    • individual (1040) or individual LLC
    • partnership/multiple member LLC,
    • corporation: C-corp, S-corp
  • set aside enough tax money: in a separate savings account
  • $600+ must report income on personal tax return (1099-MISC)
  • need 1099 from client before 2/2
  • file 1099-Misc if hired other freelancers
1099 contractor
  • double taxed as employer and employee
  • $400+ annually: pay self-employment tax in addition to income tax
  • 92.35% tax on self-employment
  • net earnings: gross income – ordinary/necessary/business expenses
quarterly estimated payments
  • 4/15, 6/15, 9/15, 1/15
  • put aside money out of every freelance payment
  • based on income history, estimate tax payments
  • rules: home office deduction – room must be solely for business-related activities
  • can deduct a portion of household expensesL mortgage interest, rent, utilities, insurance
record keeping
  • all receipts and records related to income and tax payments
working with CPA
  • ensure take advantage of all possible tax deductions and credits
  • advice on how to structure business and personal finances to lower tax bills
  • CPAs are tax deductible



  • mid 30s (M)
  • lives with gf in manhattan with pet
  • international student 
  • was working full time
  • good at managing finances: lives frugally, good financial habits


  • late 20s (F)
  • freelance designer (for $)
  • artist in resident (not for $)
  • credit card debt
  • starting to look for full time work


  • late 20s (F)
  • freelance designer/ITP resident
  • no debt
  • starting to save


  • late 20s (F)
  • installation artist/performer/freelancer (2-3 projects at a time, 3 mo each)
  • “worst person to talk about this stuff” 
  • has a lot of debt: getting nervous talking about this
  • a lot of uncertainties: just planning next 1-2 months (want to plan long term)
  • after graduating: paying off student loan
  • rent/food 


  • 30s (M)
  • graduated 2 yrs ago
  • startup experience
  • trade stocks 
  • lives in Manhattan with pet
  • has multiple accounts: personal (multiple credit cards), business, stocks


Financial management (currently)



Financial goals

Specific to freelancers

Specific to students

Specific to international students


Review: Digit

I started using Digit two week ago. After registered, I received this:


I got Digit’s message friendly and quickly. These message sounds like a good friend or a personal financial officer that reminds me how much money I have. And after few days, it started to transfer my money to a special saving account. And I still have not idea how he calculate this amount.

Unfortunately, I’m not a freelancer, my balance would hardly have change. Looks like Digit sense this and ask me to change this frequency. So I change this daily balance report into weekly by sending “weekly”.


As you can see, Digit analysis our conversation by finding keywords. And this would cause problems if I really want to chat with him. Like I said “stop saving”, Digit sense keyword “stop” and then turn off Digit message. But that’s not what I mean. This mistake prevent me from treating his as a man, it’s still a machine.


personas (?)

  • graduating student
    • Anxieties about graduation
    • Job hunt
    • Student loans
    • Credit card debts
    • Rent/food/coffee
    • Socializing: restaurants, bars, events, etc.
  • freelancers: creative, tech, etc.
    • Multiple accounts: personal and business
    • Bidding multiple projects: negotiating, contracts, budget
    • Getting paid on time!
    • Paying collaborators
    • Materials/equipment
    • Paying taxes: W4 + 1099 for different projects
  • small business owner 
    • a lot of similarities to freelancers
    • More people have business accounts: personal + business kind of blurry


2 long interviews:

  • late 20s
  • installation student/artist/performer/freelancer (2-3 projects at a time, 3 mo each)
  • a lot of uncertainties: just planning next 1-2 months (want to plan long term)
  • has multiple accounts: personal (multiple credit cards), business
  • worries about debts
  • 30 something
  • graduated 2 yrs ago
  • have startup experience
  • has multiple accounts: personal (multiple credit cards), business, stocks


Insights from interviews


  • Cut down cost, but spend on nice things (travel, big item, expensive restaurant)
  • Need to trust judgement, want to feel protected
  • Just want an indicator (total net worth) to make decisions (don’t need too specific)
  • Want all accounts in one place (personal and all projects/clients)
  • “Cannot fuck up budget” (rent, electricity, pet) vs. “do whatever budget” or “want vs. need”
  • International students have specific questions





Market research

total market

  • personal financial management app users:  12,816,140 users
  • Mobile Banking, Personal Finance, Personal Investing and Wealth Management. Your request fits under the Personal Finance category which includes: “Digital capabilities for tracking spend and income, along with budgeting.” 
target market
  • critical mass of freelancers
  • graduating students
There is also a broader market of daily money managers, CPAs, bookkeepers, private banks and others (several thousand professionals) that will manage your finances for you if you are so inclined.  The state of Massachusetts will even provide personal bookkeeping services to you if you are elderly and physically are unable on your own.
1. 87% of U.S. adults have a mobile phone.
2. 39% of adults with both mobile phones and bank accounts reported using mobile banking.
3. 22% of all mobile phone owners reported having made a mobile payment in the 12 months prior to the survey


  • mint/intuit
  • 1-2 million active users
  • people complain about bad categorization
  • troops (for Salesforce)
  • robinhood
  • expensify
  • quickbooks
  • freshbooks
  • level
  • acorn
  • goodbudget
  • wally
  • learnvest
  • quicken
  • CashPath Financial
  • Debitize 
  • Milestone
  • YNAB
Best for Individuals:
  • Mint (Lirong, Jia)
Best for Small Businesses: