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Home/The SaaS Podcast/Episode 364
Horizontal Product, Zero Focus, Then 100 Customers in 100 Days
Adam Nathan, Almanac

Horizontal Product, Zero Focus, Then 100 Customers in 100 Days

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Episode Summary

Adam Nathan built a templates marketplace that was growing fast - tens of thousands of users per month during COVID. Then he killed it. He walked away from traction, laid off team members, and went back to square one to fix Almanac's SaaS positioning.

In this episode, Adam reveals why he abandoned a product with clear product-market fit, how losing all three co-founders nearly broke him, and the 100-customers-in-100-days challenge that validated his $45 million bet on a completely different value proposition.

Adam Nathan spent a year testing ideas before landing on Almanac, a collaboration platform for remote teams. He recruited co-founders, raised $9 million in seed funding, and launched a templates gallery that took off during COVID with tens of thousands of new users every month.

But the templates gallery was never the real vision. Almanac was supposed to be GitHub for docs - a place where distributed teams could write, approve, and organize their work. The problem was that the product everyone loved was not the product Adam wanted to build.

So he made a gutsy call. He shut down the templates growth engine, let go of team members who had been scaling that side of the business, and went back to pre-launch mode. For months, Adam wandered through what he calls a fog - testing SaaS positioning angles, running ads, building landing pages, doing customer interviews - all while trying to project stability and optimism to a team of 20 people who were watching him search for answers.

The breakthrough came when Adam narrowed Almanac's SaaS positioning to living documentation for remote teams, with suggest-changes workflows modeled after GitHub. He set a goal of 100 paying customers in 100 days and hit it ahead of schedule. That focus helped Almanac raise its Series A and grow to 7-figure ARR with over 50 employees and $45 million in total funding.

Along the way, Adam lost all three of his co-founders - one to disagreements, one to mental health struggles, and one to burnout. He shares how he rebuilt his motivation, why he stopped looking for co-founders and started looking for great startup generalists, and what it takes to keep going when the person you built the company with walks away.

Topics: Positioning & Differentiation|Product-Market Fit

Key Insight

Almanac founder Adam Nathan grew a templates marketplace to tens of thousands of monthly users during COVID, then abandoned it to fix the company's SaaS positioning. By narrowing from "document editor for everyone" to "living documentation for remote teams," he landed 100 paying customers in under 100 days and scaled to 7-figure ARR with $45 million in funding.

Key Ideas

  • Almanac's templates gallery hit product-market fit during COVID but distracted from the core collaboration platform vision
  • Adam shut down the thriving marketplace and went back to pre-launch mode, losing team members in the process
  • The SaaS positioning breakthrough was narrowing to "living documentation with suggest-changes workflows for remote teams"
  • The 100-customers-in-100-days challenge validated the new positioning and unlocked Series A funding
  • All three co-founders left the company, forcing Adam to rebuild leadership with startup generalists instead

Key Lessons

  • 🎯 SaaS positioning beats feature breadth for horizontal products: Almanac's document editor worked for everyone but attracted no one until the team narrowed positioning to "living documentation for remote teams" and hit 100 customers in under 100 days.
  • 📉 Killing traction is sometimes the right SaaS positioning move: Adam shut down a templates marketplace with tens of thousands of monthly users because it represented only 5-10% of the collaboration value chain - the equivalent of Stack Overflow versus GitHub's $9 billion exit.
  • 🎯 Validate demand before building anything with SaaS positioning tests: Adam spent a year testing ideas through business plans, landing pages, and customer conversations, looking for what he calls a "spark" where people want to pay before seeing the product.
  • 🔄 Splitting resources between two products kills early-stage startups: Almanac had marketing scaling the templates gallery while engineering built the collaboration platform, effectively running two companies at once with early-stage resources - a pattern Adam calls a failure mode.
  • 🧠 Founders must project stability while navigating positioning uncertainty: Adam compared his search for new positioning to wandering through fog on a mountain - internally terrified but externally calm, because any visible anxiety would have caused his team of 20 to lose confidence.
  • 🤝 Hire startup generalists over functional specialists at the early stage: After losing all three co-founders, Adam realized the 47 people who stayed thrived in uncertainty and ambiguity - the defining characteristics of startup life that matter more than domain expertise.
  • 🚀 Content marketing creates acquisition loops when contributors share their work: Almanac recruited expert contributors who then promoted their template profiles on social media, creating a viral loop that scaled the marketplace to thousands of templates without paid acquisition.

Watch the Episode

Chapters

00:00Introduction
02:11What Almanac does and the size of the business
03:25Origin story - from product manager to founder
05:07Spending a year validating ideas before building
08:18Quitting his job to search for the right idea
09:49Why "hell yes or no" matters for idea validation
11:45Building the templates gallery as a minimum ideal product
14:23The decision to build a platform instead of a plugin
16:34Recruiting contributors without paying them
20:43How cold outreach built the supply side
22:18Getting the first thousand customers through content marketing
25:01COVID as a growth accelerator for templates
27:49Choosing to abandon a thriving marketplace
30:27The challenges of building a horizontal product
34:58Navigating the fog - searching for new positioning
36:06The idea maze and the 100 customers in 100 days goal
39:25How focus on remote teams unlocked growth
40:47Losing all three co-founders
46:25Lightning round

Episode Q&A

How did Adam Nathan validate Almanac's idea before writing any code?

Adam spent over a year writing business plans for different ideas - from direct-to-consumer wine to meditation apps - and testing customer reactions. He looked for what he calls a "spark," where people would ask to put in their credit card without ever seeing a product. Almanac was the only idea that generated that level of excitement.

Why did Almanac build a templates gallery instead of launching the collaboration platform first?

Building a GitHub-like document editor takes years - comparable products like Notion, Figma, and Airtable took 7-9 years to reach growth inflection. Adam launched an open source templates marketplace first to validate supply-side economics, build organic SEO, and teach users what the platform was for.

How did Almanac get its first thousand customers through content marketing?

Almanac ran contributor spotlights where template authors with large followings would share profiles on social media. They also launched themed template compilations on Product Hunt - like "100 recruiting templates" - creating mini viral moments. Contributors effectively lent their networks to Almanac.

Why did Adam Nathan abandon Almanac's templates marketplace despite strong SaaS positioning traction?

The templates gallery had clear product-market fit but represented only 5-10% of the collaboration value chain. Adam compared it to Stack Overflow (hundreds of millions) versus GitHub ($9 billion acquisition). Splitting resources between two products in the early days felt like a failure mode.

How did Almanac fix its SaaS positioning after killing the templates business?

Adam spent four to five months running ads, building landing pages, and doing customer interviews to find what he calls "fast moving water." The breakthrough was positioning Almanac as living documentation for remote teams with GitHub-style suggest-changes workflows - specific enough to drive ads and content that converted.

What was Almanac's 100-customers-in-100-days challenge and why did it work?

After months of searching for positioning clarity, Adam set a goal of 100 paying customers in 100 days. The narrow focus on remote team handbooks with suggest-changes workflows made marketing and sales specific. Almanac hit the target ahead of schedule, which validated the pivot and enabled their Series A raise.

How did Adam Nathan handle losing all three co-founders at Almanac?

One co-founder left over direction disagreements, another due to mental health struggles, and the third got tired of the endurance required. Adam realized his management team of ten people were better startup operators than his co-founders had been, and he started hiring specifically for startup generalist skills over functional expertise.

What did Almanac learn about SaaS positioning for horizontal products?

Even though Almanac's document editor works for any team, Adam learned that "you can never focus enough." The product only started gaining traction when they stopped saying "document editor for anyone" and started saying "living documentation for remote teams" - a specific persona with a specific workflow.

How did COVID impact Almanac's growth and SaaS positioning strategy?

COVID drove massive demand for Almanac's templates as companies scrambled for remote work policies, DEI playbooks, and async work guides. The team rapidly responded to social media conversations and republished expert content. But the surge locked Almanac into a templates-only identity, making the later pivot harder.

Book Recommendations

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by Danny Meyer

Links

  • Almanac: Website | LinkedIn | X
  • Adam Nathan: LinkedIn | X
  • Omer Khan: LinkedIn | X
Full Transcript

Omer (00:09.760)
Welcome to another episode of the SaaS Podcast.
I'm your host Omer Khan and this is a show where I interview proven founders and industry experts who share their stories, strategies and insights to help you build, launch and grow your SaaS business.
In this episode, I talk to Adam Nathan, the founder and CEO of Almanac, a collaboration platform for remote teams to write, approve and organize their docs.
In 2018, after years of working in product roles and getting frustrated with inefficient work tools and endless meetings, Adam quit his job and set out to start his own company.
He spent over a year validating different ideas before picking Almanac.
But launching a horizontal product poses huge challenges and it was no different for Adam.
When your product can work for everyone and it's easy to dilute your messaging and end up grabbing no one's attention.
And so it's no surprise that Adam and his co founders struggled to find their target customers.
However, today Almanac is a 7 figure ARR business with over 50 employees, tens of thousands of customers and $45 million in VC funding.
In this episode you'll learn why.
After quitting his job, Adam took a whole year to to thoroughly test and validate different ideas before settling on Almanac.
What the founders built first to validate their two sided marketplace instead of diving straight into building the product and it wasn't an mvp.
How content marketing and influencer promotions helped Almanac to get their first thousand customers we also talk about how Adam had to maintain optimism and and stability for his team even after losing all three of his co founders.
And what Adam did to overcome the challenges of building a horizontal product and helping his team to finally get clarity and focus.
So I hope you enjoy.
Adam, welcome to the show.

Adam Nathan (02:11.520)
Great to be here.
Thanks for having me.

Omer (02:12.960)
Do you have a favorite quote?
Something that inspires or motivates you that you can share with us?

Adam Nathan (02:17.200)
I do.
Teddy Roosevelt said, do what you can where you are with what you've got.
And I love that one.

Omer (02:22.690)
Love it.
A great quote for any entrepreneur and founder.
So tell us about Almanac.
What does the product do, who's it for, and what's the main problem you're helping to solve?

Adam Nathan (02:32.930)
Almanac is a wiki and workflow tool that makes distributed teams faster.
We save distributed teams more than a million hours in wasted work each year with fewer meetings, faster responses and less overhead.

Omer (02:43.330)
Love it.
That was one of the most succinct elevator pitches I've heard for a while.
Great.
Give us a sense of the size of the business.
Where are you in terms of revenue, number of customers, size of team?

Adam Nathan (02:57.180)
Yeah, we have tens of thousands of customers.
We're actually just coming out of beta in a couple weeks, but we've been in a years long beta period just to make sure the product really works well for our customers.
And during that time we've been able to bring on some of, I think the best remote teams around companies like Doist and Credit Karma and Adela as well as very large scaled organizations from the American Red Cross to the Emmys to.
Indeed.

Omer (03:19.420)
Wow.
And what's the size of the team?

Adam Nathan (03:21.660)
About 50 people.

Omer (03:22.620)
And revenue?

Adam Nathan (03:23.500)
We don't discuss that.
But seven figures.

Omer (03:25.900)
You're a seven figure ARR business.
Okay, great.
So let's talk about where the idea for this product came from.
So the business was founded in January 2019.
So I guess 2018 was about the time you were ready to make the leap and you know, start working on this business.
So what were you doing at the time and where did this idea come from?

Adam Nathan (03:49.200)
Well, I'm a systems engineer by training.
It's what I got my first master's degree in.
And for, I guess the eight years before Almanac, I was a product manager at Apple and Lyft and a fintech called Borrow.
And you know, I think my job, on my job description at least, was to help build products people would love.
But what I actually spent my days doing wasn't really bad.
It was, you know, sitting in meetings that were back to back, constantly looking at my slack and email to see the next hundred messages that I didn't read yet, all the while often just trying to figure out very basic answers to basic questions like what did my boss think of my idea and did the team read this yet and did I get feedback on this proposal?
And often felt like pushing a ball through mud.
It certainly wasn't work I woke up in the morning to do.
It wasn't the work I felt I was hired to do and it wasn't really satisfying.
At the end of the week, I often feel like I didn't really get what I wanted to done.
And I had this contrast with the engineers I worked with who used a tool called GitHub, which is essentially an asynchronous collaboration platform for working on code.
And the engineers on my team were way more productive than I was at actually moving the needle on work that mattered.
And they were seemingly happier.
And so I started thinking, what is it about the way engineers work that makes them so productive and so much faster than me?
And are there ways to translate that into the kind of business and knowledge work that me and my colleagues were doing.

Omer (05:07.680)
Okay, great.
So you're experiencing this pain firsthand.
You kind of are thinking about a solution.
Eventually what you want to go and build becomes clearer over time.
How did you get started?
Like a lot of people have great ideas and then go back to work.
Did you quit your job right away and start building the product?
Did you do it as a sort of a side gig and kind of work your way up?
How did things happen?

Adam Nathan (05:31.280)
Yeah, well, I'd say that the idea that became Almanac wasn't the first idea I had.
I tested, I think over a year, a whole bunch of ideas, both testing the idea and also trying to find co founders to do it with.
And I think in the pre Almanac days, the device I used was to write a business plan.
Because even though it sounds kind of quaint and anachronistic, I think a business plan forces you to think through all the elements of the business, like how are you going to acquire customers and what does it cost to serve them and what are the product requirements and what's the market size.
And so there's a bit of like background research initially just to get smart around the ideas.
I was investigating and I was looking at things from like direct to consumer wine company to like a meditation app.
So I was, I was really, I think, playing the field and you know, quickly in a lot of cases learned either the market wasn't there or was too competitive or the unit economics didn't work or it would take too long to grow.
And so that was a helpful way to narrow down ideas.
But I think the most important input I was looking for was customer feedback.
And I think with startups you want to find an idea or at least a value proposition that people react to quickly.
I compare it to dating, where if you have to find someone to MARRY on the first or second date, you want that first or second date to be not just a 7 out of 10 or 8 out of 10.
You want it to be 9.9 out of 10 or 11 out of 10.
Just sparks flying.
And that's because, you know, startups, startups are really about growing fast.
The whole point of a startup is, is to build a high growth business, especially if you're taking venture capital.
And so you need to find an idea that, you know, people almost want to buy without even seeing the product yet.
You know, they'll put in their credit card on a landing page or they follow up after you talk to them on an interview saying like hey, can I get access?
Because they're so excited about it.
And that means that, you know, you can build something that's relatively rough in a short period of time.
And, and it will grow from the start such that more investment will make it grow even faster.
And so I was looking for that kind of spark with the idea.
And I remember after trying a bunch of ideas out and not really getting that kind of feedback from customers, when I would talk about Almanac, just the idea of it to my friends, people would be like, that's amazing.
Can you do it right now so that I can start using it?
And so I had a sense of some traction there, like just electricity in people's responses.
And then as I started kind of bringing on co founders and building a team, and this is before we raised any money, I remember just saying, hey, let's put up a landing page and see if people wanted to contribute ideas or sign up.
And we just got traction so fast from so many people that the business started pulling itself.
And that was a great sign to keep moving forward with it.

Omer (08:18.710)
Yeah.
So a couple of questions.
You said you spent about a year kind of figuring out what to go and do.
Were you still working at the time or had you already quit your job?

Adam Nathan (08:29.380)
No, I quit my job.
I knew that I wanted to be an entrepreneur.
I'm an idealist by nature, so I knew that I couldn't just work on any business.
And I envy founders out there that don't really care what the business is.
They love the ownership of it or the freedom it gives.
I'm the kind of person where the idea, the vision, the mission matter a lot.
And so, and that, that, that constrained me already.
But, you know, I knew that I, I needed to kind of validate what the concept was before I really went into something.
And so I spent the year mainly looking around to try and find that spark I was talking about.

Omer (09:03.400)
I think it's interesting that a lot of founders go and talk to customers and they kind of say, I'm not sure if this resonated with them or not, or they told me they liked it, or they said it was a great idea.
And as we know, sometimes people just say those things because they want to be nice.
They.
They say what they think you want to hear doesn't mean that they're actually going to use the product or pay for it.
But there's something about what you said about the spark that when you nail the right problem for the right type of customer and you're able to articulate it in the right way, it just happens.
And then, you know, the difference in the reaction that you're getting from people.

Adam Nathan (09:49.890)
Right, Yeah, I think that's true.
The amazing thing about software today is that you can basically build anything.
And so most businesses don't have technical risk.
At least most of the time, you know, you can.
If you find good engineers and designers, you can build almost anything.
And so the real risk for startups is around the market, and whether there's unmet customer need or, you know, latent customer demand, there's.
And as I was saying, you know, most businesses don't have infinite Runway upfront.
In fact, often they only have like 12 to 18 months worth of cash.
And so you need to find an idea where essentially people want it so much that even with a average or bad product, in many cases people will buy it.
And.
And then that growth can fuel, you know, longer Runway, more investment, more momentum.
I think that there's a lot of de risking you can do around the business just without ever touching a line of code.
And I think many businesses rush too fast into building something when really I think the most important thing you can do initially is to talk to customers.
And the greatest sign of validation is someone giving you their credit card without ever even seeing the product, because that means they want it so much that they're willing to pay you money just to get access to it.
And yes, I think there's a lot of ruinous empathy with humans where we don't want to disappoint each other.
And so I think there's kind of a spectrum of validations where on one end you have, would you put in your credit card?
Would you pay me money to get access to this?
Would you refer friends to get access to this?
Would you spend time on a call with me?
There's a spectrum of validation that goes from less believable to very believable.
Certainly asking somebody, do you think this is a good idea or would you try?
This is not enough.
Because most people would just say yes.
There's no cost to that, to them to make you happy by saying that.
And so we often say if it's not a hell yes, it's a no.
And the greatest way of validating that, proving that is, is by someone paying you money.
And ultimately, that's the whole point of the business.

Omer (11:45.650)
Yeah, yeah, love that.
Okay, so you spend about a year, you get to the point where you have high confidence that you're going down the right track.
The landing page that you've built is giving you additional Validation that there is demand for this type of product.
How long did it take you to build the first version of the product and start selling it?

Adam Nathan (12:09.970)
Yeah.
So just to give you some context, our vision was always to build basically GitHub for docs.
That's what we called it initially and what it is now, where it takes a long time to build complex collaboration software like what we have done.
So initially we started with essentially a templates gallery.
It was an open source repository of best practices that people could copy and customize.
And that's very similar to how engineers code.
They often don't write everything themselves, but they borrow open source components for things like dropdown menus or login screens that are solved problems so that they can focus their time on work that actually matters.
And nothing like that we thought existed for product managers or marketers or ops teams.
You know, people were constantly reinventing the wheel and starting from scratch.
And so where we started with the business was building this open source repository of templates.
And so, you know, what we wanted to build is essentially a minimum ideal product at first.
And so we probably spent nine months building this platform where you could essentially search for templates.
All of the templates were user contributed, so we didn't pay.
They all came from experts in the field that we basically recruited and worked with to refine these templates down.
Then users on the other side of what was essentially a marketplace could search for templates and then copy them into their own private almanac workspace, which is now basically what the product has, has evolved two years later.
And so we were building the product, but really what we were doing is validating the business model, because what we had to do in these nine months were figure out how do we recruit contributors to give us templates for free, and then how do we generate demand on the other side?
And in any marketplace finding supply, whether it's, you know, drivers on Uber or, you know, reviewers on Yelp, that's the much harder side of the marketplace to figure out, because if you have supply, demand often will come.
And so in those nine months while we were building the product, we were also validating essentially our value proposition to contributors and to viewers.
You know, how, what's, what's in it for them, how do we recruit them, where are they, how do we, how do we find them, how do we talk to them, how do we convert them, how do we serve them?
And so it's a really important time for us to like, figure out how the business worked and make sure that things were things are fitting nicely before we open it up to the world.

Omer (14:23.860)
Yeah.
So one thing I want to get some clarity on is when you said you didn't have a product, you started with the templates first.
What format were these templates in and how were people using them before Almanac was ready for them?

Adam Nathan (14:40.180)
So I think we started essentially with this idea that people needed, you know, professionals needed new infrastructure for the digital economy.
That was the high level idea that tools like Microsoft Word are designed for offices and office culture.
And that now that we're all working on the Internet, we needed new tools and mechanisms that were optimized for, for online collaboration and online productivity.
And so that was the high level thesis initially.
And this is all before COVID by the way.
And so, you know, where we started was, okay, people are starting from scratch and you know, if we're all working on the Internet, all our documents are there, then we should all be able to like share and find generalized best practices.
I think we could have built a version of the product where these, these templates that I was talking about were uploaded in Microsoft Word documents or were linked out to Google Docs and then people could like copy them into those editors.
What we decided to do instead was build our own platform.
And so Almanac today is a modern rich text, real time document editor.
And inside of it there's versioning features that help you keep track of track changes.
We have workflows for requesting feedback and approvals and read receipts.
And so the idea is to in all man active data, centralize collaboration next to where you're doing the work, which is what GitHub does.
So we made this fateful decision early on rather than to basically build a plugin into other people's products to build a platform ourselves.
And so if I could go back in time and change things, there's pros and cons of both approaches.
If you just build a plugin, then another platform like Google Docs could have just easily copied our feature and then we would have been done.
The downside of building a platform is it takes a very long time and it's really complicated.
So we were not just building this templates gallery, but underneath building a document editor and along with it, all of the permissioning and the organization and navigation features that you need for a place that rewrites stuff.

Omer (16:34.610)
Okay, so they were proprietary.
But what was the.
There must have been a window between the time where a contributor who you're persuaded to go and create a template and make it available, and the time when the document editor is actually ready to be used with this template.
Which leads to the question, how are you persuading these people to create these templates?
One, without paying them?
And two, basically it was like, well, no one can use them right now, but at some time in the future they will.

Adam Nathan (17:10.250)
Yeah, it's a good question.
And just to give you some context, other productivity platforms that are like a generation older than us, tools like Figma and Airtable and Notion all took between like seven and nine years from when they started building their product to when they reached a growth inflection point.
And those are the success cases.
And so it takes a very long time to build these types of products because you have to match all the features of the incumbents like Google Docs or Microsoft Word.
Then you have to find a fatal crack in their armor that is an unmet need for enough people.
And then it all has to work well enough that people feel comfortable switching over or inspired to switch over because it's that much better.
So it's a really hard strategic play and it takes a long time to execute skewed well, yet uncompromising levels of excellence in the product experience.
And so we had started on that journey early, but as you mentioned, we weren't going to arrive there for many years.
We also made it harder for ourselves in that we didn't want to pay contributors.
We wanted it all to be like a free marketplace.
And so there was a three pronged pitch to contributors.
One was around visibility.
And so we were promising that when we launched we were going to work to generate a ton of know visibility for their work.
We were going to shower them in praise on social.
This is going to be kind of, there's profiles where they could like see how many people downloaded or copied their templates and they could use the profile to refer people to other places.
Very similar to like the value proposition of the social network.
Another part was altruism.
You know, a lot of people felt like others had helped them in their careers get to get to where they were and gain all of their skills and knowledge and they wanted to pay it forward to others.
I think largely those two things drove people's contributions.
At first we paid a small, I think maybe 100 bucks to the first 200 contributors.
But for the type of people we were getting, Gibson Biddle was the chief product officer at Netflix.
It was a fraction of what they were actually paid per hour.
And so it was amazing that we were able to gain.
By now we have thousands of contributors on what we now call the almanac Core, we were able to get them just through kind of this more altruistic message.
I think other products like Substack or Patreon have proven out that if we did allow people to, for example, gate their content and charge for it, we probably could have even gotten even more contributors.
I think looking back, that's something I would have loved to have tested.
But we were really convinced of this idea that the content had to be open and free in order for us to use it as an acquisition channel.
Most of the products I mentioned, like Notion or Airtable and Figma, they grew initially through basically building their own versions of template galleries.
Because if you're building a productivity solution, what templates help do is contextualize the product.
Like, what am I supposed to use this for?
Am I the right customer?
How does it work?
Templates are all really easy ways to do that versus complicated product marketing.
So we knew by investing in templates early, we could build like a huge organic channel for us that would rank well in SEO, over time, gain trust with customers, and ultimately teach people how to use the product.
So it was important for us to keep it free because we didn't want the templates to be the product.
A funny story is that that ended up happening.
We ended up getting product market fit just around the Templates Gallery or the open source repository, and it started to take off on its own.
We started getting more and more organic contributions, more and more visits and downloads from users, and it started to look like the Templates Gallery was going to be the business.

Omer (20:43.590)
That's funny.
How did you recruit these people?
How did you find.
And you know, was it just outbound email like you were you just called emailing people?

Adam Nathan (20:52.870)
Strangely, yes.
You know, initially we went to our friends and said, hey, would you like submit a template?
But obviously we don't all.
You know, I had four co founders, maybe we had a team of 10 people.
We don't have enough friends to get what is now, I think five or six thousand templates.
And so ultimately it had to be us reaching out to people we didn't know.
And yeah, we would cold email people with basically the pitch I mentioned to you.
We had an amazing team.
We were all working on this and we would get people on the phone and make the pitch to them and then essentially help them craft the template.
We would edit it and revise it for them to make sure that it fit our standards and that it was consistent with other templates on the site.
Then for the initial contributors is, hey, our launch is going to be In September.
So like hold on until then and then we'll ask you to help us promote it.

Omer (21:38.940)
Okay, great.
So we've talked about the marketplace and getting contributors, but this is a two sided marketplace, so you've got the other side as well in terms of actually recruiting customers and users.
How did you do that?
And maybe let's talk about the first, you know, thousand customers that you got because you've got tens of thousands of customers today.
So I'm sure the first 10 were just a lot of, you know, through your network, you know, friends, et cetera, and so on.
So I'm kind of interested in this sort of first thousand.
How did you recruit those or how did you find those customers?

Adam Nathan (22:18.750)
I think initially we had a fairly probably traditional launch to what a lot of companies did.
We launched the product on Product Hunt, we did a big press release, we raised $9 million in funding.
And what was unique about our seed round as well as our series A is that we raised from a lot of different investors.
And that was intentional to basically get a bunch of people on our side who could help us recruit contributors and then promote the product.
So we had, you know, hundreds of people basically on our investor team who are helping us share the news and you know, that helped us get to a, you know, number one spot on Product Hunt.
We got a lot of good word of mouth going.
The this is probably October 2019.
And then, you know, we, we had started to build out some drum beat organic marketing.
So we would do spotlights on, you know, individual contributors that, that submitted templates to the site who had big followings and we would do a profile on them with templates attached.
They would share that on their socials, we would share that and that would help.
That built up basically a viral loop where contributors were lending us their networks to help us find new users.
We would also do like compilations of templates on a theme, like a hundred recruiting templates or a hundred marketing templates.
And we would launch those on Product Hunt.
And that would also be basically like a mini lightning strike where we could get a bunch of attention around like a single idea for a specific type of user.
And I think that worked well.
But you know, truly the we, we saw a big updraft around Covid because essentially, you know, why would you need a template?
It's often when you don't know how to do something or you want expert advice.
And overnight in March 2020, there was a ton of things that people didn't know how to do.
They didn't know how to transition their offices into COVID 19 protocols.
They didn't know how to do remote work.
They didn't.
There was the Black Lives Matter movement in the spring.
They didn't know how to do dei.
All of a sudden people were in tons of meetings.
They didn't know how to do async.
And so basically, all of a sudden, people needed new types of knowledge from experts that they could find and use.
And so I'd say in the spring of 2020, we were seeing tens of thousands of new users each month because we started to react really quickly to the current events around us and take advantage of what we call fast moving water at Almanac.
Where is there a surge of unmet demand to try and catalyze that growth?
Businesses can grow fine at a slow rate, but would fail as a startup, because as a startup, our goal, our mission is to find this, to find fast growth, to grow at a fast rate.
And so we at Almanac are always trying to find the fast moving water.
And in 2020, it was around all these new types of skills and areas of expertise that everybody needed to ramp up on pretty quickly.
But very few people knew how to do well.
And our platform was perfectly designed for that.

Omer (25:01.470)
Okay, so you spot this need that people are searching for things that they want to do.
What did you do with that?
Were you doing like keyword research and then trying to build landing pages with different types of templates or like, how did this work?

Adam Nathan (25:19.320)
Yeah, well, at that point, we had a little bit of name recognition in the market.
But for example, in the early days of COVID 19 HR departments all were issuing guidance on like, what's, like the out of office policy, like, you know, what are health restrictions, how should communication be set up?
You know, how do we do work from home?
Initially, like, everybody needed the same types of, of documents and the same types of knowledge, and nobody really knew.
Everyone was trying to figure it out.
And there were people who were sharing free Google Docs online, people writing long tweet threads or LinkedIn posts.
And so we would basically rapidly respond to wherever we saw conversation happening on social media, Contact people who were publishing stuff, ask if we could republish it, publish compendiums of the best things that we found with some more context.
And so in doing so became like a source of truth for other people who were looking for answers.
And so we basically borrowed from the momentum and we borrowed from the credibility of the people who were organically just sharing this stuff because they also wanted to help, which was, as I said, Very aligned with our value proposition to grow our user base.
A funny thing happened along the way, which is that we became known as essentially like an open source repository of documents and as a, in other words, a templates gallery.
And all the while we had this bigger vision around becoming a collaboration platform.
We were building this document editor, we were building these workflows to be like GitHub.
I think a truism in startup is that you only get product market fit, for one thing.
And so people began to know Almanac for being this open source repo and where you go to find answers on pressing questions in this brave new world of work.
And so that meant our users weren't like just taking the templates and then using them to collaborate privately in their own workspaces.
They wanted more templates for us and they wanted more template features.
And so because we got product market fit around the templates, they wanted more and more of the same.
And we were like, no, we want you to come and do this other thing.
And they were like, no, no, no, what you're doing, what you build is great.
Can I have another?
And so we face this choice of do we continue to build and scale this product that clearly had traction, but that wasn't the thing we wanted to do, or do we make a hard pivot and essentially abandon the customers and all the value we had created around the templates gallery, or at least kind of put it on ice so that we could focus on shifting our value proposition to what we thought was a much bigger economic opportunity.

Omer (27:49.350)
How did you make that decision?
Because you had something that seemed to be taking off, you know, a lot of potential, a lot of opportunity, and yet you decided basically to put that on the shelf.
It's still, the site is still live, right?
People can still go and access the templates.

Adam Nathan (28:08.480)
Yeah, it's still, it's still there.
I mean, it's like, I think any.
Obviously we, we abandoned it.
That was the decision that we made.
The, the volume of Tempo's growth, you know, basically flatlined as soon as we, as soon as we did that.
And of course that meant that the overall quality of the site started to degrade.
People would come back to it and say, like, hey, why haven't there been any new templates published?
And you know, 5 months, 10 months, 12 months.
And so.
And so just as there's a virtuous cycle in a marketplace where as you get more supply, you get more demand, there's also a vicious cycle where as supply degrades, so does demand.
If you look at what's happening with Lyft right now.
It's a good real time example of this.
You need or even Facebook, you need both sides to be moving in concert.
The flag for us is that we were basically splitting our efforts.
You know, we had most of the marketing team focused on growing the Almanac core, but most of the engineering team was focused on building this collaboration platform.
And so we essentially were trying to build two companies at once.
And we knew that especially when you're in the early days of growth or when you've just achieved product market fit, it's so hard to do one thing well that to split the difference in the early days seemed insane and like a failure mode.
And so we realized we had to pick a path.
We couldn't do two things with the resources that we had.
And we thought that we looked around at, I guess, benchmarks in the engineering space.
Again, Stack Overflow is a several hundred million dollars business at scale.
GitHub was bought by Microsoft for $9 billion.
And so there was like 100x difference between having a value proposition around where teams collaborate and do work versus a value proposition of where teams find answers.
Finding a template is maybe 5 to 10% of the value in the collaboration value chain being the place where work is composed, where it's revised, where it's published is probably the other 90%.
So I think it was an easy strategic choice, much harder to implement.
We had to let go of some people on the team because we had started to build out this marketing team.
As the templates gallery scaled, we had basically GMs or verticals who were recruiting contributors and managing the content.
And we basically needed to shift, you know, from what we were doing at the time, which was like scaling this business to go back a couple steps to essentially pre product market fit, pre launch to focus on the collaboration platform.

Omer (30:27.990)
That had to be a hard decision, I'm sure, like if the template marketplace was doing kind of averagely well or whatever, maybe you could be like, yeah, let's kind of walk away from that.
But so let's talk about some of the challenges that come with building a horizontal product.
And that's exactly what you're doing with Almanac.
But the problem is who do you focus on?
If you just say, I'm building a product for everybody, that really dilutes the kind of features you build, how you build them, your marketing, your go to market, all of that stuff.
So tell me about, firstly, tell me about some of the struggles or difficulties you had building a horizontal product and Then how did you approach it?
How did you focus and try to nail the types of features you were going to build, your marketing message and all that stuff?

Adam Nathan (31:29.560)
Yeah, well, I think I learned the hard way that the startup truism that you can't ever focus enough is, is a rule that applies to everybody.
And I think just to go back to the context here, you know, we had built this templates gallery and even that was hard to even know there because we had templates across all sorts of functions, like who really was our customer, like who wanted this more than anybody else.
And I don't think we had a good answer with the templates gallery.
I think the eventual answer was remote teams because they needed, you know, a whole bunch of new types of knowledge and best practices to figure out how to work in this, like at the time in the pandemic era environment.
So we basically had a foothold around remote teams.
And I'd say on the core the remote category dominated all the other categories.
I think product management and engineering was a close second.
But then we basically kind of go back to pre launch again where we're building internally, we're building a much more complicated product around a document editor.
And because we're pre launch again, pre product market fit, kind of going back to those days, we had to re answer these questions of like, who is this product?
For what benefit does it deliver, what does it replace, how is it better or different?
And it's really hard to answer those questions if you don't have a lot of customers because there's too many options to start to cross them off the list.
And so it took us a really long time to figure out a methodology to do this.
It almost feels, I think initially like boiling the ocean because it's like, where do you start and how do you know that it's a no?
And I think in a startup the early days are really about momentum.
Like startups are fueled before the field on revenue by momentum.
And so the trick is to find product market fit before the team gets tired and everybody leaves to go do something else that's newer and more exciting.
And so like, I think when we kind of pivoted and, and went back inside, the team is a little bit dismayed.
Everybody saw the long road ahead of us and we didn't have answers to these questions of like, who's our target customer?
What's our value proposition to them?
Why?
Why are we going to win?
And I felt like I was on borrowed time to try and figure it out before we started losing critical members of the team.
And so that was a really scary period for me, and I think for everybody, especially for me, because unlike what we talked about, you know, when we started the business and we had that sense of, like, spark or traction that where we were being pulled rather than pushing, all of a sudden, it felt like I was.
I compared it to a fog.
Like, I was walking up a mountain and, like, through a forest, and I couldn't figure out, like, where the path was.
I lost the scent, and I was just kind of, like, wandering around, like, trying to.
To find the scent, but not.
Not so frantically that I would scare everybody else.
But it was a.
It was a really, like, dark period to try and figure out, like, who.
Who wanted this thing.
And because I could turn in any direction, and if you go in the wrong direction too far, you've lost critical time.
You have to backtrack.
And at this point, it wasn't just me.
It was a team of 20 people who were actively doing stuff.
So there was a cost to every wrong turn I made.
And I think a lot of founders who kind of pivot midstream find themselves in this position where it's not no consequence like it is when you're just.
Like it was for me in 2018, when I was just contemplating ideas on my own.
We're spending money, and people have dedicated their time to work for us on our team.
And, yeah, it was not fun.

Omer (34:58.709)
It's tough.
And I'm so glad that you shared that and that analogy of the mountain and the fog and stuff, because it's such a tough journey for any founder, and you don't want to tell the team what you're struggling with, because that's just going to make them lose confidence in you.
But that is such a great analogy in terms of just a snapshot into the difficulties and the challenges and the decisions you have to make, while at the same time keeping everybody excited and motivated and moving forward and hopefully towards the.
Or in the right direction.
How long did it take for you to maybe not just figure all of it out, but at least get to a point where, going back to your analogy, you felt like you could see a path again and felt that this was the one that you were going to follow for a while and hopefully it was going to lead to the.
The right outcome?

Adam Nathan (36:06.310)
Yeah, it probably took four or five months.
And Chris Dixon calls us the idea maze, where you have elements, like pieces of the puzzle, and you're just trying to figure out how they fit together.
And so I knew, okay, we Have a bunch of people who we found traction with because they're newly remote teams and they're trying to figure out how to work.
I knew some of the templates that people most wanted were standard operating policies and procedures.
So I had some sense of like, okay, there's demand around this, there's fast moving water on this.
You know, we were building a product that was a document editor with version control and workflows very similar to GitHub.
So it's like, here we have this asset.
How do we, like, what's the best use case for it?
Again, this would have been better if we were doing this without a team, but we basically went back into customer validation where we were quickly putting ads out of market to see like, you know, where we could get low, low CPCs.
We were building landing pages to see who would sign up to them.
We were doing customer interviews, we were testing stuff on social, just like basically quickly trying to figure out, like, where is there a pulse in the market?
And you know, when you do that for three or four months, it starts to wear on the team, like, are these guys ever going to figure it out?
And of course everyone looks to me as a CEO for to understand, like, are we okay?
And so if I don't look okay, especially on public calls, if I look worn down or scared, like everybody else is like, oh man, we're screwed.
And I remember finding it just really difficult to like separate my internal feelings and anxiety and fear and stress from the stability and optimism I needed to portray to the team.
And I remember, you know, it's always darkest before dawn.
I remember one of my co founders, it was like December, I guess, 2020, and I was in Hawaii on vacation and one of my co founders was like, I don't think this is going to work.
And I was like, no, I think I have it.
And the idea was to basically portray our.
We called it living documentation to take the document under rebuilt, make it a source of truth for customers, especially remote teams, and use the workflows that we had built to enable anybody to suggest changes to those documents so they could remain trusted for everybody.
Unlike a Google document where anyone can go in and edit it and you don't know, is this the final version?
Can I rely on this information and almanac?
Everything was locked down, but there was like these protocols where people could suggest changes through track changes or comments that then would be approved by the document owners.
So very similar to how GitHub works, but for remote teams.
And so I was like, I think this is It.
But of course, it's still just kind of a hypothesis.
So we decided kind of as a.
As a next step to try and get 100 customers in 100 days, 100 paying customers.
And then we thought if we could get 100 customers in 100 days, we could certainly get 1,000 customers after that.
And we thought if we could, that would be a sign that we were on the path to product market fit.
And so the first quarter and second quarter of 2021, that was our goal, like 100 customers in 100 days.
And we did it.
We got 100 customers way faster than 100 days.
And I think that speaks to the benefit of focus, where rather than saying, hey, we're a document editor that can do anything for anybody, we are really focused on building handbooks with suggest changes for remote teams.
And that value prop.
We built ads and did a lot of social and organic content around that value proposition.
And we started just racking up customers, and that enabled us to raise our Series A.

Omer (39:25.400)
All right, so in many ways, I mean, the product is horizontal, but you still made a bet on a customer or type of customer that you were going to focus on.
And I love this idea of 100 customers in 100 days.
And then once you've picked that customer and made the bet, everything sort of gets behind that, right?
Like the marketing message and, you know, what, what you're.
The features you're focusing on and things like that.
I want to talk about the situation with your co founders.
And I know you said to me, hey, I don't want to spend a bunch of time on this, and that's fine.
I respect that.
So I don't want to kind of go and dig for dirt or, you know, but you started out, you know, you started out by yourself.
You went through the process of finding co founders, and eventually there were four of you, and now you're back to one person again.
Tell me, at what point did the other three co founders end up leaving the business?
Was that around the time of this pivot or before or later?
And what kept you going?
Because suddenly the journey becomes a lot harder, I think when you're dealing with all of these struggles and you're the only founder left who has to figure this stuff out

Adam Nathan (40:47.040)
Initially, I actually wouldn't start Almanac or any of the ideas I had without co founders because there's oft repeated advice that starting a business on your own is a really bad idea.
And so I was obsessed with finding co founders who would be committed to the long journey with me.
And so I had the idea for Almanac.
I was getting traction for it maybe like four or five months before we actually incorporated the business.
Because I wanted to find co founders first.
And this was in 2018.
You know, I was getting introductions to people, meeting with them and we would go through a pre mortem exercise that was like, basically preferences for the business.
Like, what's your role going to be?
What's my role going to be?
When will we sell?
Do we want an office?
You know, how do we make decisions?
How do we divide up equity?
And so interestingly, this exercise is pre mortem took a bunch of people who I thought would have been great co founders and made us realize that in fact we like, were in a line a lot of things to probably save me first from some, some bad relationships.
And you know, co founder is interesting because it's, it's like a romantic partner that you're like, in that you're spending all your time together, but you're also like completely like financially committed, like without diversification.
Like, you guys are both in it, in it together.
And so it's like even more intense than a romantic relationship, I think.
So.
So finding.
I was initially really committed to finding great co founders.
Ironically, as you mentioned, none of them are with the business anymore.
One left within a year because we just had differences of opinion about the direction the business was going.
Another left because he was suffering from a lot of mental health issues, which he's written about publicly.
And the last, I think, wasn't interested, got tired and wasn't interested in, I think, the endurance it would take to achieve our vision.
I think that last one was really difficult for me because this was like my greatest fear that I would be alone.
And it was the thing I said I was my red line.
Like, I don't want to start this alone.
And then all of a sudden, like, I was alone.
I was all my co founders had left.
And, you know, I think two things helped me.
One, I realized I actually wasn't alone.
You know, we have a management team at Almanac of ten people who are perfect for, for running a startup.
And, and I think that's the hard thing to know when you're starting a business is like, is this person actually going to have what it takes to make it all the way in a startup?
And you know, you might think that they do, they might think that they do, but the only way you really know is when you get into it, like not, not in the first mile of the race, but when you're on, like mile 45 and you're like, okay, we're in this now, we can't turn around.
But like we're nowhere near the finish line of like a, you know, a hundred mile race.
Like, that's when you figure out what people are made of.
And I think the greatest success I've had at Almanac, more than our revenue or our customers or what we built, is that I have found a group of people who are purpose built to work at a startup and have exactly what it takes to not just succeed, but knock any startup idea out of the water.
And when we recruit people at Almanac now for any position, what we realized is we're not just looking for people who are great product managers or product marketers or engineers.
We're looking for great startup generalists.
There's a specific set of skills that make someone good at the startup stage, and that's actually much more important than, you know, whether someone's excellent at their function.
Because the definition of a startup operating environment is uncertainty and ambiguity and change.
So you need people who like, not just can tolerate that, but love it and get energy from it and thrive in it.
And, and so, you know, we over time had built a team at Almanac full of those people, almost exclusively of those people.
And so the three people I found initially weren't, weren't those people, but I've now found 47 people who are.
And so I'm lucky to be surrounded by, I think, the right people at this point, that, that, that will go the distance with me.
And I think the second thing is, like you said, I had to kind of reconvince myself about why I was doing the business because again, I crossed this red, this red line I had set for myself.
And so I was like, well, do I want to do this anymore?
And so I think two things that convinced me, and this was maybe last year, were the same things that convinced me to start a business in 2018.
One is that I don't think there's any other thing I can do.
I think my unique strengths are a perfect fit for founding and running a business.
I think those same strengths would make me maybe intolerable in other contexts and other roles, but they make me really good at my job.
And so I don't think that there's anything else I can do as well as I do this job.
And two, I love our mission at Almanac.
We published something recently called the Modern Work Method, which is essentially like agile for business.
It's a compilation of all the things we've learned working with thousands of customers about how to work well on the Internet.
And it's essentially our theory about the future of work.
If you want to work well and fast as a remote team, there are better and worse ways to work.
And here's what we learned about how the best teams operate.
And as I said, I'm not someone who could just start any business.
I'm a systems guy.
And figuring out how people work well or poorly is the ultimate systemic challenge.
And what we get to do at Almanac is build tooling that helps people work better, work faster, work more efficiently, work with more happiness.
And I love that it's the ultimate challenge and puzzle, and it's stimulating and rewarding every day.
And I love that I get to be part of it.
And so getting back to my why of why I'm doing this in the first place, I'm not doing it to have co founders.
I'm not doing it to raise money.
In my case, the wealth doesn't even really matter.
I'm doing it because I love the problem that I get to work on, and I love the people I get to work with, and that's more than enough.

Omer (46:25.780)
That's a great answer.
Thanks for sharing that.
All right, let's wrap up.
Let's get onto the lightning round.
I've got seven quick fire questions for you.
Just try to answer them as quickly as you can.
Ready?

Adam Nathan (46:37.740)
Sure.

Omer (46:38.300)
What's one of the best pieces of business advice you've ever received?

Adam Nathan (46:42.300)
Be prepared.

Omer (46:43.420)
What book would you recommend to our audience and why?

Adam Nathan (46:46.220)
Setting the Table by Danny Meyer, who runs the Union Square Hospitality Group.
The book is about running a restaurant, but I think serving people in a restaurant is very similar to how you serve and care for customers in a startup.

Omer (46:59.370)
Great pick.
What's one attribute or characteristic in your mind of a successful founder?

Adam Nathan (47:04.570)
Grit and persistence.
Never giving up, even when you'd long be okay for doing so.

Omer (47:11.210)
What's your favorite personal productivity tool or habit?

Adam Nathan (47:15.370)
Going to the gym and working out.
It always clears my head and helps me see things better.

Omer (47:20.410)
What's a new or crazy business idea you'd love to pursue if you had the time?
And if you don't have the time, somebody can steal,

Adam Nathan (47:28.440)
I think some way to figure out loneliness, which I think is an epidemic in modern society.
And on the other end of the spectrum, opening up a cocktail bar.

Omer (47:35.800)
What's an interesting or fun fact about you that most people don't know?

Adam Nathan (47:39.960)
I was a competitive skier.

Omer (47:41.800)
Oh, you?
Really?
Wow.
I didn't find that in my research.
And finally, what's one of your most important passions outside of your work?

Adam Nathan (47:49.720)
I chair a nonprofit board here in San Francisco that's working on the homelessness and addiction crisis.

Omer (47:55.440)
Awesome.
That's great.
All right, that's a wrap.
So, Adam, thank you so much for joining me and sharing your story and your journey in building Almanac.
I really appreciate you taking the time.
If people want to learn more about Almanac or check it out, they can go to Almanac IO and if folks want to get in touch with you, what's the best way for them to do that?

Adam Nathan (48:17.120)
I think my DMs are open on Twitter.
People are still using that.
Or I think my email address is all over the Internet, so you can always email me, too.

Omer (48:27.290)
Okay, that's great.
Thanks, man.
Appreciate it.
And I wish you and the team the best of success.

Adam Nathan (48:32.490)
Thank you.

Omer (48:33.210)
Cheers.

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Tito Goldstein, Teambridge

Finding Product-Market Fit After 2 Years of Almost Nothing

Tito Goldstein is the Co-Founder and CEO of TeamBridge, a composable workforce operating system for hourly workers that serves over 500,000 employees across 200+ enterprise customers. Tito Goldstein and his co-founder Arjun were two of the first principal product designers at Uber. After interviewing thousands of Uber drivers worldwide, they realized something powerful: drivers were choosing Uber despite lower pay because of the agency and self-service the app provided. They raised a $3 million seed round to bring that same experience to the 60% of the global workforce who are hourly employees stuck with legacy tools. But after building their initial scheduling product, they hit a wall - two years of near-zero revenue and no product-market fit. The problem wasn't the market. It was the product. Customers kept saying they needed to stand out, not use the same cookie-cutter software as their competitors. Their secret sauce lived in spreadsheets and manual processes, not in a fixed scheduling tool. So Tito and Arjun made a gutsy call: throw out the scheduling product and rebuild as composable Legos. Customers could start with a template but configure 20% to match their unique workflows and differentiators. The new product outsold the previous two years of efforts in the first month. Product-market fit had arrived. Then it 3x'd, and 3x'd again. Today, TeamBridge powers NFL stadiums like the 49ers' Levi's Stadium, medical staffing agencies scaling from zero admin staff to multimillion-dollar businesses, and enterprises managing thousands of hourly workers with self-service automation.

How Repositioning This AI SaaS Unlocked 7-Figure Growth - Flo Crivello

Flo Crivello, Lindy

How Repositioning This AI SaaS Unlocked 7-Figure Growth

Flo Crivello is the founder and CEO of Lindy, an AI SaaS platform that lets anyone build AI agents to automate workflows without code. In 2020, Flo Crivello was running TeamFlow, a virtual office startup that raised over $50 million. But when people returned to offices, growth flatlined. With no path forward, Flo pivoted to build Lindy, an AI SaaS platform for building AI agents. The idea came from his sales team asking if AI could automatically update Salesforce. Flo kept climbing the "ladder of abstraction" until he realized he was building an AI SaaS agent platform. In March 2023, he launched with a demo video that generated 70,000 waitlist signups. But the AI SaaS product was terrible. It would send emails that literally said "the user wants me to send an email to 50 software engineers." Users were surprisingly forgiving because they understood they were early adopters. Flo's breakthrough came from repositioning. His AI SaaS started as "AI employee" - too futuristic for the broken product. He repositioned as "Zapier of AI," making the AI SaaS accessible by positioning against something familiar. Within months, Lindy hit product-market fit and grew to high 7-figures. This episode covers the brutal reality of pivoting an AI SaaS, why familiar positioning beats visionary messaging for early adoption, and how to know when your AI SaaS has reached product-market fit.

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