I'm Aleem Mawani, Founder and CEO of Streak. AMA!


Hi everyone! I’m Aleem Mawani, CEO of Streak .

I previously worked at Google and then founded Streak in 2012. Early on we raised a small seed round but have been profitable since and haven’t raised more capital. We have a tight knit 25 person team and recently celebrated crossing $10M ARR.

Streak provides a CRM service deeply integrated into the Gmail experience. Our primary customers are SMB teams and founders looking to manage their sales, hiring and fundraising processes. Our competitive advantage is how we’ve made email the first class citizen of a CRM - both in the user experience and where we automatically pull data from.

Happy to talk about:

  • going from big company to founding a startup
  • hiring
  • how we build product
  • our fundraising strategy
  • our failures and obstacles we ran into
  • how to do your best work
  • whether an MBA is worth it

I’ll be back on October 14th at 9:30 AM PT to answer as many questions as I can—looking forward to it!


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) :brain:

(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 :open_book:/:headphones:

(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


Hey Aleem,

Thanks for doing this! " 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." As I read your thoughts on that I can imagine how liberating it can be for founders to acknowledge this but it is very hard.

Also, it was great reading your thoughts on carving a third path for startups. You’re absolutely right. I think the possibility of building something large and profitable has only increased lately with access to newer financial instruments and economical tools.

Still a core part to get right, even with a longer time horizon, is distribution. You’ve mentioned how initially ~90% of Streak’s users came through the Chrome web store. A channel that was repeatable and scalable. Sort of under-leveraged when you were getting started.

It’ll be really useful to hear how you’ve thought about diversifying channels there on while being mindful of profitability as a core value. Have you continued looking for similar slightly riskier, under-leveraged channels? Especially as you’re also selling to much larger teams now.


Hey Aleem,

I second Krish. Streak has taken a rare (shouldn’t be so :)) and remarkable path. Loved the idea of building just one thing that’s 10x better while being 10x worse at other things.

Aside from the Gmail CRM, you’ve also built an email client. Which is, always has been, a huge undertaking. Curious to learn how the 10x principle applied to that. What did that first delivery scope document looked like? And how should early-stage founders think about what that first 10x-better piece might be?


Hey Aleem,

Thanks for taking the time!

Such a great journey to read about.

You’ve mentioned somewhere how now you aren’t focussed on building a “billion dollar business” and instead being intentional about first being a $10m company, then a $50m, then a $100m company and so on. This is really intriguing.

  • What does this entail? Or rather what were some of the core operating assumptions that changed when you made this mindset switch?
  • For the $10m and beyond path that you’re on, what are some of the mistakes from the previous phase that you’re aiming to address now?

@aleem Hi Aleem, thank you so much for taking the time to do this AMA! It’s so inspiring to hear your story. I have been aware of Streak for a long time – you’re the real deal – a proper “OG” SaaS business!

Thanks for sharing your story and also for sharing the path you’ve been on.

I am curious, having taken some investment early on – did you proceed to buy out your early investors with profits, or are they still with you and supporting you?

I agree wholeheartedly with you that ideally there would be a better way to build a successful SaaS business that doesn’t hit the binary “fail” or “unicorn”.

Also, seeing as you suggested it as a qu: is an MBA worth it? :wink:


Had another one in mind, Aleem. :slight_smile: How has the definition of ‘doing your best work’ evolved for you as a founder, over the many phases that Streak has been through?


Hey Aleem - thank you for taking the time. Would love to know some of the closely-held beliefs as a founder that you had to let go of as you went from 0 to 100K USD to 1M to 10M USD?


Had to ask this, given your time at Google. :)) From an operating principles/operating rigour perspective, what were some of the “big-company” lessons that you have continued to observe at Streak?


Thanks for the question! Our first channel was the Chrome Web Store because it was completely underutilized (high traffic, low number of good apps). Since then thats changed and its been less and less of an important channel for us.

Our biggest channel is word of mouth, and it’s not surprising - our passion is building a good product and our customers tend to tell others about that. Another thing we spend a lot of time on is product led growth (although it wasn’t really called that when we started!). Specifically we offer some free tools (Email Tracking, Mail Merge, Share) that can all be used independently of our CRM, are more focused and are all free. The idea being we give away some free tools to attract new users, and some of those users eventually discover our CRM and convert to paying users. Approximately 10% of our current paid users were just email tracking users first before using our CRM. We have a really poor user flow from these tools to our CRM so we’re investing a lot more here (better flows + more tools).

We’ve also recently started looking at paid channels. Podcasting, SEO, SEM, LinkedIn, Twitter… all the usual suspects. We’ve found some pockets of profitability but we’re def in the early stages and haven’t scaled any channels yet - more of an investigation!


Ahhh building an email client. Yeah we had to do that on iOS and Android. Well, we didn’t really want to build one - like you said its a huge undertaking. Our hand was kind of forced because on mobile, our users still wanted the deep email integration. I’d almost say this was an area where we just had to hit a min bar at and didn’t really contribute to our 10x better advantage. In fact, we so didn’t want to do this that in our initial versions we just embedded a webview in our app and pointed it at gmails mobile website. We injected some JS into that webview to get the deep integration with Streak - it wasn’t pretty but it worked. Barely.

That being said - our longer term vision is for Streak to be the way users do email. And building an email client will be a big part of that. Our new iOS app thats in beta currently makes some huge strides here - the email client is better than Gmail’s.


I think the main thing was that we never thought we needed to raise a bunch of $$$ and hire a huge team to get to our goal. Because our goal was 10M or 50M or… we just had to make it to that next step.

That being said, it can sometimes lead to an underinvestment in things that take a long time to execute on i.e. executive hiring, ops hiring. Those are some areas we need to invest more in now even though we can probably get to the next step without it. It just makes the step after that even harder.

We clearly need to build out a larger supporting organization. We were very scrappy getting to this point but like I mentioned, we need to hire better in finance, ops, marketing, etc.

It’s also much harder to move the needle now given the base is so high so finding scalable marketing techniques vs taking on every random opportunity will be important.


Yes. Because of the unique shape of our business (growing & profitable but not unicorn) it didn’t fit the needs of some of our investors. For those, we did buy back their investment. For others, they were fine sticking around and seeing where it headed. Def appreciate all the support we’ve gotten from all of our investors, but sometimes the company and investor needs change.

I mean, I was mostly trolling :slight_smile: . 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.

The network I’ve built has already led to opportunities that have returned the tuition “investment” many times over. If you can minimize the opportunity cost of an MBA (by starting your biz at the same time, its a no brainer).


My role has changed a bunch in my time at Streak. I’ve literally done every single role. On the positive side, i think it’s easier to hire for a role when you’ve done it before. On the negative side, the role outgrows you quickly and I’ve def stayed too long in a role and done it a disservice. For example, I built our first backend and our first iOS app. I should have stopped at that and let the pros take over - I continued coding and became a bottleneck on our team.

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. Those 3 things are usually different. The goal is to try an align those as much as possible (though you have to know it’ll never be 100% overlap and that each of those factors are moving targets).


In 2007, Google’s management techniques were still relatively “startupy”. So all of those have applied at Streak:

  • flat management hierarchy
  • daily snippets of what you’re working on
  • 1:1s
  • consistent perf reviews (although we do them more frequently)
  • bonus structure

Most of the engineering principles, product development, and strategy from Google mostly hasn’t applied at all.


That’s well put, Aleem! It’s tough. As an extension to this, what are some personal habits and routines that help you stay sane as you think through constantly making that alignment?


Leaders at the company all post in a slack channel weekly what the single most important thing they want to get done that week. That makes the above tradeoff very clear.


Going from $5M-$10M we really had to investigate churn and directly address it in a rigorous way. Before that we were just building product we thought new users wanted us to have. Over that time we were able to get churn down by almost 70%.


Thanks so much for doing this, Aleem! :slightly_smiling_face: 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. :raised_hands:

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Thanks, Aleem! You’re right. The PLG concept hadn’t been coined back then. It’s great to learn that Streak has had product-driven growth all along. And I feel the idea of deploying free tools as acquisition channels also remains largely under-leveraged; so it’s quite fascinating to hear that you’ve had success with many such adjacent tools at Streak.

…balance what the company absolutely needs from you vs what you’re good at vs what gives you energy

Ha! The fine line we all tread, so well put!