What were your first coding gigs, and how did you get them?

"I’d love to hear more regarding how quickly you went from novice to earning your first dollar from programming, how you found these first gigs and if you’d take the same approach if you were doing it all again."

there's an idea floating around that one cannot charge $$ for their coding skills until they are "proficient." let proficient be the ability to write code with similar ease as writing a blog post.

this is false.

i began picking up freelance clients long before i was proficient in programming. to deliver those gigs each feature was just as painful as completing a tutorial. the key difference is i was paid to learn.

first gig

  • amount: $1,500

  • learning for: 3 months

  • spec: utility that validates a California resident's "medical marijuana" legal status (yes seriously)

  • how i got it: no clue... was taking a walk around 9p on a weeknight and got a call from a random number... guy heard about me somewhere, can't recall where

coding is about breaking up big problems into a bunch of tiny problems that can be solved with "true" or "false."

the client pointed me to a government website where one can punch in a person's full name and medical ID number, then click Verify. on the following page was a "success - valid" or "error - not found" type of message, along with a green or red background respectively.

my client gave me some sample names + IDs for testing, so first i simply used the website like a normal person, in the browser. i then noted the differences described above... red background + "not found" vs green background + "valid."

i cracked open my Ruby terminal and read a few pages of documentation on watir.com. within 20 minutes i was filling out the government website form, browser-free, and geting back a page of HTML.

next i browsed documentation for scanning text with Regex and was able to parse out whether a results page was successful or invalid.

finally i deployed this to Heroku with a free boilerplate rails app, dropping the code into a service file and attaching a form input (HTML) to the "lookup" variable in my script.

within 90 minutes i had a working checker that handled bulk "lookup" of California resident medical marijuana eligibility. my client cut the check, ecstatic.

second gig

  • amount: $3,000

  • learning for: 4 months

  • spec: SMS newsletter platform for an ecommerce wine shop

  • how i got it: perhaps Angel.co? emailed founder, pitched ideas, and "gulped" when they said yes

i was way over my head with this gig, but i probably 2x'd my coding chops while building it.

since i was already working full-time at a venture capital firm i think version 1.0 took about 3 weeks. then i spent another couple months improving it, and we switched from the $3k flat fee to a monthly retainer. so, probably made closer to $10k for this project over 4 months.

basically i built "Mailchimp for SMS," which tapped directly into the ecommerce store's API and synced customer records.


  • admin, aka "Somm on Demand," could log into the tool and build a custom audience with dropdowns

  • admin could blast a text like "Hey {{ first_name }}, we have a bottle of XYZ for 50% off! Reply to order!"

  • shopper would reply "3" or "5" or "how does it taste," etc, and admin could automatically process payments using credit card attached to customer account

  • every shopper had a "profile page" with a notes area -- basically a lightweight CRM -- so admin could keep tabs over time

  • shopper's entire conversation thread was always available in-app, and admin could text back/forth (1:1) with a bunch of shoppers simultaneously, all from the website interface

at one point this app drove several thousand dollars per month in sales, so i think it was a win-win for all parties.

third gig

  • amount: $2,500 (i think!)

  • learning for: 5 months

  • spec: cold email generator that drives qualified traffic to a cold email SaaS tool

  • how i got it: casually introduced by a former boss years prior, then asked to hang out at the office

since this project is public, i'd rather "show" than tell:


Cold Email Generator

#1 Product Hunt app of the day, 100s of leads, ranks #1 on Google, yada yada. fun to build and forced me to learn more JavaScript! until this point i was primarily focused on Ruby.

fourth+ gig

once you build a few things, and particularly after you capitalize on them with a Projects page, you'll have more inbound leads than you can handle.

i spent the next couple years toggling between paid (contract) vs personal (passion) projects, as well as continuing my studies (on and off) via online bootcamps.

there are still many things i don't know, but today i am "proficient" and make more $$ than i ever thought i was capable of.

if you want me to teach you to code, go here.