It also wouldn't have solved his problem. VC money in this case would have been like putting a bandage on an cut artery. It'll slow the bleeding temporarily but someone still has to sew things up at some point.
In this case, it's not something to outsource or forget about even when raising money since cashflow management just becomes more complicated and increases the risks of opaque numbers catching up and killing the company when the runway ends.
Growth/product are not nearly the major challenges in business, unlike what Silicon Valley likes to keep repeating.
Fascinating company to follow, an "overnight success" after years of hard work. Look at that MRR go https://convertkit.baremetrics.com/stats/mrr#start_date=2013...
I remember hearing about Nathan and ConvertKit years ago on patio11's podcast when they were discussing pricing. Congrats on bootstrapping to some impressive numbers, don't forget to enjoy some of the benefits now!
It's been my general experience that startups, especially startups built by dev-focussed folk, tend to radically underestimate the impact of people issues (moral, amount of sleep, work/life balance, etc.) on their effectiveness of their business.
In fact I saw almost exactly this story, but with dev rather than support. Going from _perception_ of their being an ever growing list of new features, massive overtime, general feeling of being overwhelmed. To showing that folk were actually getting on top of things with numbers. To some scope adjustment so we could make the hours sane. The team getting happier, and faster at every step.
The other thing is we had focused our entire 5 person dev team on helping support with bug fixes and help text / documentation for common problems. That took a while to kick in and lower the support load, but it's definitely helped!
You can solve a lot of problems through better time management, more efficient processes and improved focus.
Nathan's book Authority led to my creating a website from my books in 2013, and it's grown handily. I currently have the opposite issue: my revenue growth slowed, but expenses are low so I have a largish runway. Recently started investing more in capital and look to be on a path to grow revenue with a new product very shortly.
Specifically a Macbook pro. I had been trying to launch an initial video product using a macbook air, figuring I'd buy the better computer once I had proven revenue. But that delayed me for months due to technical slowdowns. I bought the pro last week and will probably have a very minimal product out this week.
Slack's been a big help. Several years into the business my processes had gotten too complex and it was slowing progress.