I bootstrapped projects for 8 years and recently raised $2.75M in VC funding. AMA!

Hey @psto! Thanks for the question. I replied to someone else about the funding question in why we decided the Arrows company specifically needed funding, but I'll add a little extra:

One thing I found as an "indie hacker"/bootstrapper/self-funder myself for many years was that much of my identity as a builder was wrapped up in that. I didn't actually have a problem with VC funding, but I found myself really having a difficult time with it. And I feel ultimately that it was a self-limiting belief at that time in my life.

However, I have zero regrets and am happy with how I've built things. They all helped set us up to be able to go after this opportunity now.

---

The most surprising insight that we had really came around researching what problem to solve. Simply put: all work that people do at companies is like plumbing. It's a series of workflows, inputs and outputs, pipes that connect.

So to understand what problems someone has, you need to step through everything they actually do so you can understand where the headaches and inefficiencies are. Then when you build your product that solves one part of that workflow, you also understand the nuanced details of the steps that come before and after that part of the workflow... When we talk to customers, we really try to dig into what happens around the work they're doing in Arrows so we can better understand how to help them do the work inside Arrows.

I started to write about it here and hope to add to the series: http://arrows.to/resources/building-arrows/working-in-bets/

Hey @dqmonn ;-)

We recorded an episode of the podcast about this (the one about raising funding): http://arrows.to/keep-going/

But the simple answer is: we realized the product category we're in and the customers we're serving necessitated us having funding.

Our customers and sales prospects have really high expectations of what the product can do, and it was not a great signal when the founder was the one doing sales calls (which is often the case as a boostrapped company). Many companies don't want to buy important customer-facing, revenue-driving tools from two dudes who might not be around in a year or two... they want to feel more confidence.

On the other side of that, we thought hard about what products make for good bootstrapped businesses, and we found that typically they were going one of two routes:

1. They were an opinionated or niche-focused product in a very large existing category (i.e. Convertkit with email marketing. There is a major market here with large incumbents). This means there are a lot of people looking for something like your product already or customers switching off existing providers (i.e. mailchimp/others) because they're unsatisfied.
2. They're building products specifically for a niche and the market isn't big enough to support a lot of companies, but customers look for and buy that specific thing.

Arrows was and is trying to serve a broad set of customers, but we're in a new category that still needs time to develop and build awareness. We got real with the facts and realized we needed to become the Salesforce (#1 in size) of this category so that eventually a Highrise (smaller niche product) could exist later.

@codegeek1001 Great question. That was one of the big reasons we avoided taking funding for a while... we didn't have a good answer for what we'd do with it or what it would unlock for us.

Primarily it's people. We have two engineers that started yesterday, so we can build a lot more of what our customers want a lot faster. We also hired one of our earliest advisors, someone who we've now been giving to our own customers as a free consultant on customer success and onboarding best practices. That's been hugely beneficial. And we hired sales + design, so I as the CEO am not in charge of those anymore as well.

I don't have less work to do now... it’s that Arrows as a company can now parallelize more processes and deliver faster for customers. If anything, I have more work.

Otherwise, it's been great to run more experiments and make more bets on things like ads or content marketing or hiring a contractor to help us with our Salesforce integration without the risk of any of those failing and it feeling like a waste of money.

This is a fantastic question @mirv, and one I talk about often with friends.

Simple answer: no. I have zero regrets.

I am happy with my life and my choices, and I don't have any reason to believe I'd actually be happier with more money but without the friends/partner/Arrows/etc that I have in my life right now.

More complicated answer: yes, I wish I would have stayed at Twilio another couple of years and learned more about that next stage of growth. OR that I'd have gone to Stripe and learned a lot about scaling a different company (and I wish i had closer friendships with the early Stripe people I knew). Yes, having the money those people have would be great, but it's not the primary reason I wish I'd have done them.

haha Thanks @dternyak!

hahahah @itsTimConnors

Thanks for the kind words, @disrael! We're all set right now but I'll send it to the team!

Hey @harriskenny!!! One of our favorite customers 💘👋🏼

I've found the most popular episodes to be surprising. Often we found the 3rd episode being one of the most listened to, long after we recorded it, because it was about filling up our sales funnel. Makes me realize we should record a follow-up about it.

Otherwise, the funding episode and our episode with our PR consultant were the most reacted to... but typically we don't get a major response. I've meant to ask for it more. haha

Here's our top episodes sorted by total downloads: