I’m Arjun — CEO and Founder of doola.

doola started 3.5 years ago after originally getting into Y Combinator with a different idea.

It was a video messaging app — TikTok meets Gmail. Instead of us being on a live call you could send a short Instagram story.

We thought this was perfect during COVID — but it turns out people don't really like filming themselves for messages.

People were fine with Slack or Zoom — It wasn't a tenfold improvement. We deferred demo day and shut the company down. 

During the pivot process we realized that even though we didn’t know what to build we were going to have to pay lawyers $30k again to restart our company.

For us it was even more cumbersome than for most people because our corporate entity was based outside the US and we had to convert it to a US-based one.

That gave us this idea of this business in a box or a one-stop shop where you don't just form a company and then feel like you've been thrown to the wolves with a checklist of things to do. 

Instead you get a trusted long-term partner to run and grow your business.

Now we've served over 10k businesses from over 167 different countries across 6 continents.

The pre-seed round was YC plus a couple other micro funds — including Hustle Fund.

We got the YC standard $250k investment at the time, plus some other checks. It ended up being about $500k for the pre-seed.

After YC we did end up participating in a deferred demo day, followed by raising our seed round. We secured $3.5M with a valuation of $13.5M.

Then a year and a half later we did our Series A — which was $8M at a $40M valuation. 

For the seed round, part of our goal was to raise capital to build out the product suite. At the time we had several hundred thousand in ARR.

As a first time founder, I didn't know what I didn't know. I might think some amount is enough, but an investor would say, “hey, you might want to take a little more.”

That's how we settled on those ranges in both cases.

It’s a very tough thing to actually do because they're taking a bet on you as much as you are with them — It's like dating or meeting someone. 

The first meeting is probably too soon to pull the trigger, but you also don't need to do 3 years of it. There's a happy medium, which is likely at least a few meetings. 

The biggest sign — and I've learned this the hard way — is if someone is interested there's naturally going to be more speed.

The way you respond is natural biology. If you aren't interested, you're going to lean back first before you actually say you’re out.

I've learned that the hard way — speed's actually the best leading indicator.

In terms of how to choose, there might be times when you don't have options. You need someone to believe in you — beggars can't be choosers. 

The ultimate goal is being at a point where you actually don't need the investor.

If you're profitable — or on a path to being profitable — then you are naturally going to have more leverage and approach conversations accordingly.

It's especially very tough when you're going to get a ton of no’s. I've looked at our investor CRM and there's been over 100 people who have passed.

Some of our first investors were just cold outbounds. One of our earliest investors I DM’d on Twitter.

Others were post-YC demo day. Others were through intros from existing investors or other folks too — it was a mix.

The interesting thing has been that — from that first round of investors — there's been interesting ways that future folks have come in either as customers, partners, or investors. 

Someone who initially wrote a really small check introduced someone who ended up writing a much bigger check or helped us in another way.

You don't realize the importance of that initial person at the time.

I don't have the exact funnel from back then, but Elizabeth Yin from Hustle Fund has this great concept — the rule of 60.

I might be getting the exact number wrong but the concept is that it takes that many convos to get a single yes — for us, the number was 30.

We ultimately ended up doing over 100 cold outreach emails and it translated to maybe 30 to 60 conversations.

Those conversations resulted in 20 total investors — over a couple of rounds.

I made a CRM 3.5 years after starting the business — I should have done it sooner. I set it up because I had no system. 

I realized I was losing track of everything — I think I spent a full day going through all my emails.

Now it's really cathartic because I don't have to think about it. I know exactly where I am with all investors for when we are ready to fundraise next time.

Any time I get any investor type of communication it goes right in there.

People know our market is huge because there's millions of SMBs globally and many of them will eventually either need to come to the U.S. — or are already in the U.S.  

But it's a leaky bucket business because they don’t like to spend a lot of money.

How do we acquire a lot of people in this competitive space? Company formation is a challenging wedge even though it's a clear pain point.

The biggest risks were figuring out some way to cut through the noise and stand out.

Once the customers sign up we can then expand the amount they spend by offering them relevant, supplemental products.

We emphasized our ability to stand out in our pitch. Part of that was me building up my personal brand on social media — but there’s obviously a lot more that goes into it.

If someone is interested they will move fast. 

Something I say to the team all the time is that the sale is made in the follow-up. People get busy. You can't expect one email. You have to bump it to the top of the inbox.

If someone still isn't moving, the silence is a sign because they would be interested in moving on the other side.

I was relentless with my follow up, but also paid close attention to those organic signals.

The biggest question we get is “why can't someone else do the exact thing? What's the differentiator here? Is this going to cap out at a certain point because it gets too competitive?”

These are all completely valid questions. Our response is demonstrating how we go to market quickly.

Another question is about churn.

For that we just show that our core users stick around, love the product, and that there are enough of those people to build a big business around.

The value of YC as an investor has translated to sales.

Recently a customer said that they were hesitant, but because they saw we were a YC company they instantly trusted us.

Don't raise anything more than you need. This forces you to actually build the business. 

Take some cushion because you never know what can go wrong, but you don't need too much cushion just for the sake of doing it.

Fundraising doesn't equal building a business. Your customers don't really care how much you have — they care if the product's good.

If you're not getting a lot of no’s you're probably not doing it right — or the idea is too consensus.

This might mean that it's too competitive and there's no moat or potential differentiation.

This doesn't mean it can't be a business, but you might run into hurdles around investors seeing it as a venture-scale business.

Also don't limit yourself to warm intros, but also don’t do 100% cold outbound — you should do a bit of each.

Try a little of everything — you're increasing your surface area for getting lucky.

You also don't need to reinvent the wheel on many things. If systems have worked for other folks, use them.

If there's any takeaway here, a CRM and a system is good — even if it's a spreadsheet it's better than nothing.

I'm a big fan of YC. That can sometimes be a divisive topic, but the way I view it is that the odds of you getting to the next level are irrelevant — you either get there or you don't — so take the help you can get.

As first time founders there's so much you don't know. 

YC has seen lots of companies. There is some basic pattern matching of seeing 100 companies make the same mistakes.

We wouldn't be where we are today without YC.

A book I wish I read when we were starting was The Great CEO Within by Matt Mochary. 

Matt was a CEO coach for Reddit, Brex, Coinbase, and other companies too. It's such a tactical, action-packed book. 

Each chapter is a specific playbook. I've read it multiple times and there's still things that haven't been incorporated.