Sahil Lavingia

Very impressive Miles ! You should speak to Sahil http://sahillavingia.com/ Wish you all the very best !

For what it's worth Gumroad left VC land several years ago. https://sahillavingia.com/reflecting

One of my predictions/hopes is that part-time work becomes far more prevalent. In addition to the benefits already mentioned here, it would be great for people who want to be e.g. entrepreneurs or independent researchers. Wrote a bit about this here: https://jacobobryant.com/p/what-im-trying-to-do/#1-help-build-a-career… Also relevant: https://sahillavingia.com/work. I'd like to make a collection of part-time success stories like this.

If your software business relies on last minute availability all the time, no engineer worth their salt will work there. https://sahillavingia.com/work

Gumroad is such a great model of company in my opinion: https://sahillavingia.com/work HN dicussion back then: https://news.ycombinator.com/item?id=25673275

The most important consideration here is whether you want to take VC funding at all, or bootstrap as much as possible. There are many fine businesses that fall into the VC game, have undue pressure to hit hockey stick growth and hire too fast. If their strategic prospects are limited, you end up having to downsize and restart. This essay changed my perspective https://sahillavingia.com/reflecting Not saying this model is right for you, but worth a consideration.

Sahil wrote a blog post about the length of emails: http://sahillavingia.com/blog/dont-judge-an-email-by-its-length/ There are other questions and answers that you should check out. My favorite: Q: Rails or Django? A: Users don't care so I don't care.

I agree with the above statement that it is insanely busy and distracting and packed with too much tiny text. There are lots of interesting portfolio/resume pages out there, I like Sahil's for one: http://sahillavingia.com/

sahillavingia, your personal site looks awesome too! http://sahillavingia.com/

I appreciate the kind words! The second part of your post is something I've thought about a lot. There are a lot of incentives driving business operators to try to get the most out of the fewest number of employees possible: - Less communication overhead due to fewer people - Constant availability (less need to pre-plan meetings, etc to match everyone's hours) - Less complexity WRT HR, payroll, taxes - Employees still have to pay for full healthcare, so the employer either provides this or pays a 1099 salary premium (the US's terrible approach of tying health insurance coverage to your employer rears its ugly head yet again) - Fewer SaaS seats to pay for Some of these are more solvable than others, and allowing more people to work part-time in tech is definitely swimming upstream, but I do wish more businesses would try. Sahil Lavingia (Gumroad) is one person leaning into this approach with great success: https://sahillavingia.com/work

> It wasn’t always this way; from 2015-2019, everyone at Gumroad was paid cash, no equity. No one wanted any. Gumroad started in 2011 and raised $8 million. The reason "no one wanted" any equity in 2015 was because they laid most employees off, replaced them with contractors, and the investors wrote their equity down to $1 as a gift to the founder. The founder got to keep the IP, ditch the founding employees, and continue running the company. The founder wrote a couple articles about the experience: https://www.businessinsider.com/startup-failure-gumroad-why-startup-fa… https://sahillavingia.com/reflecting What's not pictured in these articles is the employee perspective. The founder got to keep his company, got the company's IP handed to him, and I don't know what became of the employees' equity. Probably nothing, given that the company had to be written down to nearly $0 for this transfer. I remember reading a very angry Twitter rant from an ex employee who was burned. I wish I could find it now, but that was nearly a decade ago. It was one of my cautionary tales about taking equity in startups at the time. It hadn't ever crossed my mind that someone could take VC money, pay employees (partially with equity) to build a company, then everyone gets laid off, equity declared worthless, but the founder gets to continue operating the company at a profit. It's also interesting to note that the Tweets embedded in both of those articles above come from Austen…

Disclosure - I don't know Sahil and have never had any interaction with him or Gumroad except as an ocassional Gumroad customer. I find this take to be disingenuous at best and outright misinformed at worst. Sahil has been very public with what happened [1]. Gumroad turned out to be a lifestyle business and not a VC funded boom or bust rocket. He could have easily shut down Gumroad and gone on to bigger and better things. He persevered and today Gumroad has risen from the ashes and creators are better off for it. Kudos to him and his motley crew. He has extensively blogged about it and been public about Gumroad's finances. Maybe one day Gumroad will be worth $1B but it is a long road ahead and I wish the new investors the best. Back to Sahil's actions, unless you have actual instances of wrongdoing by him, I feel you are just flinging innuendo. [1] https://sahillavingia.com/reflecting

I think it is the opposite - it is a consequence of which system has better long term surviveability. Companies survive because they don't die. That seems trite, I know. The consequences of it are important, as the equation is one where no matter how well you do, avoiding death is what matters. SHL at Gumroad is a great example. SHL was encouraged to quit by the VCs when Gumroad was not a clear unicorn[1]. SHL chose not to let Gumroad die, and Gumroad lives. The problem with all the ideas like the one Yanis Varoufakis proposes, is that they will almost certainly do well in good times, but companies survive because they don't die, and any system like the one you mention will lead to more dead companies. That's a big claim I know, but imagine a situation where a company has 20 people - 4 sales and 8 support (secretaries, returns, admin) in the office and 8 people who work in fulfillment - a warehouse and lets say deliveries. Times get tough, and they are forced to have a vote on who needs to be sacked - how do they vote? 12 of the 20 work together, do you really think they will vote to have their friends in the office sacked? And would they even get to that point? Why would anyone ever vote to lose their job? And what about pay rises? How do you negotiate pay rises when everyone votes? In a multi-division company, lets say 3 divisions, would everyone vote to take a lower pay than people in a more productive division? Would hiring be run along profitability lines, with one…

sahil also said: > "The public was seeing news reports of mass firings that seemed cruel and heartless, many assuming DOGE was directly responsible," he continued. "In reality, DOGE had no direct authority. The real decisions came from the agency heads appointed by President Trump, who were wise to let DOGE act as the 'fall guy' for unpopular decisions." He also only very briefly worked with a single agency (VA), and his positives comments were about how the VA already had some open source Github repos and had a previous project to 'reduce claim times from "133 days to under a week"'. He was also critical of how they don't fire people with seniority, regardless of performance (which is enshrined in a reduction-in-force law from 1944) which is why new and probationary employees were the ones let go. https://sahillavingia.com/doge

Diary: https://sahillavingia.com/doge Repo: https://github.com/slavingia/va

Sahil bought out the investors and wholly owns the company now: https://sahillavingia.com/reflecting (search for "New beginnings")

Gumroad's journey has been interesting: https://sahillavingia.com/reflecting -> Billion dollar journey with VC backing to Kleiner selling back their stake to Gumroad for $1, which enabled Sahil to steer the company in a different direction. Perhaps the shift to making the source available has more to do with work culture: https://sahillavingia.com/work

Agreed. Their 'no full time employees' philosophy would be consistent with that: https://sahillavingia.com/work

To be fair, this is a small software firm that famously runs lean, and has been outsourcing junior-level work to contractors for a while. See: "no meetings, no deadlines, no fulltime employees" https://sahillavingia.com/work I can totally see AI-assisted code editors being more effective than back-and-forth with a contractor to define a job

Have you read Sahil Lavingia's blog? https://sahillavingia.com/reflecting

Gumroad has one FTE (me) and 21 part-time contractors. I write more about it here: https://sahillavingia.com/work It was a natural outgrowth of working remote and then async to lean on the hourly contractor model. It’s a little tough to scale, so we built some custom software to do payroll, contracts, etc: https://flexile.com

Here's an article by Gumroad's founder that covers how many employees Gumroad has: https://sahillavingia.com/work 25 people work at Gumroad, but none full time.

May be look for jobs that offer reduced working hours? For example, quoting from https://sahillavingia.com/work >People work at Gumroad as little as they need to sustain the other parts of their lives they prefer to spend their time and energy on: a creative side-hustle, their family, or anything else.

I wouldn't have dared to think of something of the sort till I came across Gumroad's philosophy: https://sahillavingia.com/work > It seems counterproductive for anyone to look for a part time dev when there plenty willing to work full time for the same H1B opportunity. If you're a small company, you're going to have a lot of difficulty hiring a senior engineer who's had experience building highly scalable systems or systems with similar unique characteristics. Being open to a part-time position could give you leverage & result in a win-win situation.

I thought they contracted out their entire staff? Seems that “keeping their workforce happy” goes against contracting. If you do a contract and you like the client, you might pick up another one. Otherwise no hard feelings, get the current contract done and go work for someone else. https://sahillavingia.com/work

>, he continued running the company with new part-time employees, I think he continued with part-time contractors instead of employees if I read his blog post correctly: https://sahillavingia.com/work > Instead, I found an Indian firm called BigBinary and hired a few engineers as contractors. >These contractors saved the company. They fixed bugs and maintained the site while I answered support tickets, designed features, and wrote about new initatives. [I'll delete this post if it's inaccurate]

After reading the article on Gumroad's way of working, I was really impressed that this kind of model functions so well at this scale. [1] The first question I had was are there more companies that work in this way? After searching, I discovered that I'm not the only one. [2] That's why I've just launched Creator Jobs which has a goal to collect different companies that support Gumroad's model. [3] If anyone knows other companies that work in a similar way, please feel free to comment or reach me at [email protected]. [1] https://sahillavingia.com/work [2] https://news.ycombinator.com/item?id=25686678 [3] https://creatorjobs.co/

I just created http://unaffixed.com for finding and posting Gumroad-like jobs [1]. It's just a markdown file converted to html and served from a Fastmail folder. My process was: Read this thread [2] yesterday afternoon. Thought this sounded like a "looser" work environment. Searched "synonym loose". 3rd result was "unaffixed". Bought unaffixed.com and pointed it at Fastmail. MD to html with pandoc. Added water.css stylesheet last night. Thought up some ideas on making it better. [1]: https://sahillavingia.com/work [2]: https://news.ycombinator.com/item?id=25686678

this article about how gumroad works was at the top of the front page yesterday. https://sahillavingia.com/work discussion https://news.ycombinator.com/item?id=25673275

I believe he's referring to this article[0] which was discussed on HN yesterday. [0]: https://sahillavingia.com/work