Note: This AMA is closed for new questions, but you can check out the existing conversations below.
This October 14th, we’re stoked about hosting Streak’s founder and CEO, Aleem Mawani. With Streak’s decade-long run, Aleem and team have brilliantly exposed (and departed from) a long-held startup binary. The often needlessly-hyped, towering grandness of the be-like-Google-or-die, VC-backed efforts vs the often falsely-assumed inconsequentiality of leaner businesses. They’ve instead sought the rarer, middle path of building a large, growing, and profitable business.
AMA Index (Aleem’s brain-pickings) 
(Hard-won insights, opinions, and observations; thoughtfully examined and articulated)
— Acquiring users with free tools, word of mouth, and PLG (before it was a thing!)
— Notes on building an email client from scratch
— Getting to $10m, $50m, and beyond, a step at a time
— Streak’s unique investor situation and why an MBA might just be worth it: “If you can minimize the opportunity cost of an MBA (by starting your biz at the same time, its a no brainer).”
— “As a CEO it can be tough to balance what the company absolutely needs from you vs what you’re good at vs what gives you energy.”
— Some “startupy” management techniques they’ve borrowed from Google
— Reducing churn by almost 70%
Further reading/listening/pondering from the interwebz 
/
(Other insightful excerpts drawn from blog posts, interviews, and conversations)
On diffusing their platform risks (with Google!):
A big risk and a question we got asked all the time was, ‘what if Gmail just builds this’? That’s platform risk.
This is the area where it was helpful to know the team and the strategy at Google. Which is basically, they’re not interested in vertical solutions. They’re interested in ‘how do I get the next billion users?’
They don’t get to the next billion users by having these specialised, vertical use cases. So we knew it wasn’t really a platform risk for us.
From the outside people thought it was a platform risk….You should definitely know the people on the platform team.
Because people don’t realise, it’s really easy to talk, especially for founders who’re like, ‘how do I know what Google’s thinking?’ Just go talk to them! They’re people. Just like anybody else.
…
The other risk with these platforms is, what if they change their products in a way that’s not aligned with your product. So, one worry about Gmail is like, ‘oh what if they change in a way that there’s no threading, no conversations, and whatever.’ And you build your product with that mindset.
And what derisked this for us was that we know email has been around for thirty years. Kinda hard to like really innovate on the model. There’s a bunch of people trying but like it’s pretty clear that the list of conversations is kind of the model.
Source: Boost VC | 2020
On discovering the third, uncommon startup path; being large and profitable
I used to think of startups as like very, very bimodal, and like that is kind of is in the conventional wisdom, that you either get massive like Google-massive, or you die.
Like those are the two options. And I think the thing that would have surprised me back then was that there is this third option of being a large, growing business that is profitable and making money but not necessarily like Google-size. And that’s like a great place to be.
…
I think we got really lucky. We got the opportunity to raise some money, so we didn’t feel the pressure at the beginning. We had the chance at going big in 18 months, not that we’re not going to go big in a longer time horizon, but we had a chance to go big and that didn’t happen.
The alternative wasn’t zero for us. The alternative, instead what happened, was we failed according to the VC model, but the alternative was we created this large, profitable business instead. That was the failure-mode, a large profitable business.
And large, profitable, and growing software business. And so like, I think that’s an option for – I think with SaaS it opens that option as like, there basically needs to be a new model for, ‘Hey, yes, you can raise money and attempt to go to the billion outcome in 18 months, but if it doesn’t work out here’s this other option.’
Right now there isn’t a clean way to make that transition. We kind of got lucky making that transition but there isn’t a clean way, for example, with investors of like how you make that transition. There is no convertible note that says, ‘Hey, if you end up becoming a large, profitable business instead, here is what happens to the note.’
Right, like all the financing docs and stuff like that are built around if you go huge, here’s what happens and if you die, here’s what happens.
…I think that’s an option and a lot more founders would start companies if they knew, that like, they could still go big, and if not, they could still be a large, profitable company.
Source: IH | 2020
On being 10x better at one thing:
We were 10X better in one area. In a bunch of other areas, we were actually 10X worse. We were really bad at most things, but in this one specific area, our Gmail integration and how deeply we integrated with the UI of Gmail and the backend of Gmail, that experience was kind of sublime.
It’s kind of more common now, but back then it was kind of a revelation to see that, like, ‘Oh, the place where I’m doing all my work is also the place where I am tracking all my work.’ That part of it was definitely 10X better. So, when people emailed us, they were like, ‘Hey, we love the product. We’re totally sold on the Gmail thing, but you can’t even take notes, you can’t make a date column. I can’t record a dollar amount and you have no support for currency. How am I supposed to use you as a CRM?’
A lot of those things we still haven’t done to this day because it’s more important to be 10X better and the way I think about it is that the first phase of product development is that 10X-better phase. Then the next phase is getting all the rest of the stuff to meet a minimum bar.
So, we spent a long time. CRM is kind of a product where there are so many features that people just expect and I think email clients are kind of like this as well. Building email clients is so hard because there are so many features that people just like, depend on like, ‘Oh, I need mute threads, I need to have email signatures, I need to have all these things and multiple inboxes, and split panes.’
And so, to even build an email client with your one unique insight, you have to build all these other features just to get people to use it. So, we spent a lot of time after building that 10X feature just getting decent at all the other stuff.
Source: IH | 2020
On deciding when it’s time to start charging:
I think it depends on who your customer is, if your product is for enterprise customers, you start charging from day 1. Because you want to know whether you can sell this thing.
That wasn’t us. We were almost a consumer play. Like single two-user deals. In which case, it’s more about, ‘can you reach enough people?’
And then charging is sort of secondary. For us, because we’re building a CRM, we’re basically saying, ‘hey, what’s the risk that we won’t be able to charge them later?’
For us there’s no risk at all, Salesforce charges people $120 bucks a month. I’m sure we can charge half that. I’m sure we can charge a third of that.
I’m not worried about people not paying, people are used to paying for CRMs, I’m not worried about that. I’m worried about, ‘can we build a good product?’ ‘Can we get this in the hands of customers?’
So for us it made sense to be free for a while. And then charge. In retrospect, I think we were free for a little bit too long. But I think the general advice is that, is it a risk to your business that maybe you won’t be able to charge people money?
Source: Boost VC | 2020
How has the definition of ‘doing your best work’ evolved for you as a founder, over the many phases that Streak has been through?
. For the most part I think it’s worth it, especially if you start your business while at school. You can directly apply some of the material (not much) but more importantly, you can make use immediately of the network you’re building (with peers, professors, alumni, etc.). Plus everyone wants to help a student out.
Great to learn about the ideas and figures (and their very startupy interplay) that have informed Streak’s unique path. And thanks to all the Relay founders who could make it with an excellent set of inquiries. 