There are a *lot* of software shops in the world that would far rather have one more technical dependency than they'd like to pay for one of their 20 engineers to become the company's SPOF expert on the joys of e.g. HTTP file uploads, CSV parsing bugs, PDF generation, etc.

Most software founders, particularly in B2B, need to get radically better at sales. @Steli , who is the best person for explaining the scrappy stages in the beginning and then building out a team with scripts and processes, wrote a guide to:

For technical founders it is irrationally, obscenely hard to reverse years of programming (ba dum bum) that sales is a value-destroying activity. Sales is CLEARLY a value-creating activity, contingent on you have a value-creating product.

The world will not drop what they are doing to adopt your work. This is particularly true in B2B, where simply building a better mousetrap won't overcome the activation energy required to get people with additional non-mice problems to prioritize changing mousetraps today.

This is very non-obvious for founders because founders are not often people who *want* to be sold to. We often come from a background where trying out tools is a bit of a fun hobby. We like looking at all the options, making charts, and ripping out partially complete tests.

"This week I unsuccessfully trialed four software options for automating that thing that has been killing us. Our actual production process remains the same as last week. Don't worry; this was a great use of time." is not a thing you want to write in a progress report to manager.

My friends @robwalling and @einarvollset just launched TinySeed, an accelerator for software companies where a successful outcome is a healthy, sustainable business rather than attempting to ride the rocketship trajectory. https://t.co/LSHqZNcVid

I have some thoughts:

As somebody who bootstrapped ~4 companies, I feel like I had to make some clearly suboptimal decisions early in them for lack of what is, in hindsight, not all that much money. But there's a huge gap in the product space for investment options.

It's weird: you can get $25k from Amex trivially, and angels are very willing to write a check for that much, but you have to make representations about your goals/ambitions/market/etc which don't really apply to everyone.

And so you see the traditional angel/VC ecosystem fund companies where honestly the returns are probably not there, and this is knowable pretty early, but the chase of them will wreck what could have been a perfectly happy business.

(To make the math work for traditional VCs the company has to at least have a market-appropriate shot of $100 million a year. There are a lot more $10 million a year companies than $100 million a year companies. That is *not* a bad terminal outcome for founders/employees.)

One of the big promises of software is composability. You can build rich, powerful experiences out of basic building blocks.

APIs add new things to the toolbox. For example: Treasury, which lets an app/platform store, move, and track a business’

I've been a small business owner and can talk at length about SMB banking, and will later, but let's put on the software developer hat right now.

Lots of software talks about money, keeps records about money, does calculations about money, but can't *touch* money.

This is extremely frustrating when you're building SaaS apps for businesses, because you have total control over your UX right until your app needs to touch money... at which point all data about it lives in a silo you can't access.

So you generally push work to the operator.

For example, suppose you’re writing a business-in-a-box system for electricians, including an invoicing feature.

You need to be able to read bank transactions to reconcile. You probably can't. The owner can. So you ask the owner to do mind-numbing work a computer does better.

It sure would be great if your business customers had bank accounts you could actually introspect and operate on their behalves! You could just get the list of incoming payments and match against the invoices.

There is some software to write but it is not rocket science.

A thread on HN about bad code in legacy projects both makes me think how little we've learned as a discipline over the years and, honestly, how little credit we give ourselves for some pretty major

Fun going down this list and thinking: "Hmm, plausible at a well-run modern software shop", "Hmm, possible, but requires implausible tradeoffs", "Literally disallowed by languages", and "If you were to attempt doing that our test suite wouldn't let you merge."

I think we as an industry celebrate (not quite the right word) failure too much and don't celebrate success nearly enough. There is no DailyWTF for competent execution, word of which generally stays pretty local to the source while incompetence passes into legend.

Alrighty let me try to thread the needle on being the change I want to see in the world while not giving away anything that will get me in trouble:

Ruby has wonderful developer ergonomics. Typed languages are easier for machines to guarantee the correctness of. We built a type checker for Ruby (and I believe it is slated for OSS release sometime).

c.f.

Torn between "I think losing $100 million when someone beats you at security research is pretty much exactly what you signed up for doing yield farming" and "Maaaaaaaybe not the future of finance you were expecting, huh."

How to put this in regular finance terms...

Suppose hypothetically you have an account at a brokerage with some valuable asset in it. You take a margin loan against that asset to fund your normal spending, or pay a tax bill, or maybe buy something at another brokerage.

For reasons known only to the brokerage, they don't denominate your loan in dollars. They denominate it in shares of a money market fund, which are worth $1 +/- epsilon and basically never deviate from that.

And you think "Hmm, I have a large equity cushion against this loan."

One day, a computer system at the brokerage reports, sorta-kinda erroneously, that the value of the money market fund is actually $1.30 per share. The equity cushion is gone. Your valuable asset is sold, at timing you didn't choose, at wrong price, to pay an inflated phantom debt

And your recourse is... probably tweeting at patio11 saying he finds too much joy in this.

Which I don't; I just feel like this is why you don't trust a CPU built out of redstone to build reliable financial infrastructure on top of.

At Udemy, we were 3 first-time entrepreneurs trying to raise seed capital. We made every mistake in the book.

We got 200+ no’s and wasted 12 months fundraising.

We eventually pulled through, just barely. 😅

This thread shares our mistakes as lessons for founders.

**Read On**

We built an impressive product, but we were nobodies.

We thought: we need money to build our vision, so let’s go talk to some investors.

WRONG.

Nobody gave a fuck that we needed money. We needed to prove we deserved their money.

We met some associates and intermediaries who might introduce us to investors.

Few decision-makers wanted to meet with us.

We should’ve stopped there.

If getting meetings is hard, it will take you forever to raise.

Instead, spend your time building product + getting traction.

I was frustrated with investors: treated them as adversaries who asked dumb questions. My derision turned them off.

Learn to understand and appreciate investors. Follow them on Twitter, listen to podcasts from @HarryStebbings or @eriktorenberg.

An investor's job isn't easy.

They kiss a ton of frogs just to find one deal that may make them money 10 years from now.

They only win if you become a billion dollar company.

Don’t kid yourself - if you aren’t the right fit, bootstrap.

Risk-adjusted, bootstrapping can make you happier and more successful.

I'm doing an AMA on @IndieHackers.

Drop some questions in there! Happy to answer anything, esp around building side projects with a full-time job :)

https://t.co/da4Ael9TnE

My high level plans for Starter Story.

On almost quitting

cc: @daviswbaer

@daviswbaer How I find so many businesses to interview

@daviswbaer On balancing different projects

1/ Thread: "A Silicon Valley Ponzi Scheme"

Thanks to @chamath for laying this out in Social Capital's 2018 annual letter.

I've always appreciated his outspokenness.

2/ The hardest thing for most startups today is the path to market: first finding product-market fit & a way to reach customers, then building a ruthless machine to acquire, monetize & retain them.

3/ Because of this, when the VC industry invests capital into fast growing startups today, the plurality (if not majority) of invested capital will go into user acquisition and ad spending, for better or worse— usually worse.

4/ Todays massive venture-backed advertising, sales, and user acquisition playbook has morphed into one that champions growth at any cost.

This is creating a big bill that will soon come due...

5/ Ad impressions and click-throughs are bid up to outrageous prices by startups flush with venture money, and prospective users demand more and more subsidized products to gain their initial attention.

What I learned from raising my first seed round.

This isn’t a how-to guide, that may come later. This is just a story and observations from my own experience.

See, I didn’t know what I was doing at all...

We had a built a prototype, people seemed to like it. Investors seemed to like it. Not because I showed it to them, I wouldn’t know how to do that.

But I got a lot of inbound asking about the product and found myself stumbling into meetings with people with no real goal.

We decided it was time to raise and I had to figure out how to do that.

I’m not from SF. I’m from small town Missouri. I didn’t have connections.

But I did spend a lot of time making internet friends. It’s what I’ve done my whole life. In particular friends in @genzmafia

It was here I had some help from @nhuebecker on the first pitch deck I ever made. It went a long way btw - Thanks nick!

And met a lot of connected people thanks to @ItzSuds. He also got me on clubhouse.

In there I started talking to people and met @YousifAstar

Yousif taught me the game. I cannot stress this enough he taught me everything. Pitching, materials, intros, down to the verbiage of my emails.

He taught me how to be intentional with raising instead of stumbling into meetings.

I blocked off two weeks and got started.