(Image of the investment deck I put together for SaaS Weekly.
We all have our past lives
This one quote still haunts me:
After navigating my own founder journey, I now see why this quote resonates with so many people.
We all have our past lives. Whether you leaped from big tech to a startup or you’re working on your next venture, the mistakes we made and the lessons we learned shape what we focus on. Ideally, the intuition and frameworks you picked up help you avoid the most common pitfalls. Those experiences then become the foundation for future wins.
Ideally…
However, that wasn’t the case for me. I’m only left with a scorecard of losses and a tally of lessons.
The story of my past lives
I’ve had multiple startup flops (which I share below), each with their unique learnings.
I also sat on both sides of the table, as an investor and an operator. In one of my past lives, I invested in growth-stage SaaS companies and helped to advise their GTM strategies. I also have a year of operating experience, executing growth plays to scale a B2B SaaS startup.
All of these past experiences shape what SaaS Weekly is today. The perspective I gained is deeply rooted in the content I curate, the opinions I share, and the takeaways I deem important.
With that being said, I thought it’s important to give the backstory of why the publication exists in the first place. Hopefully, this sheds light on why I care about the content and what influences the roundups every week.
The road to SaaS Weekly
A tale of two failed startups
I found that words are easier to sell than code.
In my past life (I’m not that old, 25 actually), I would spend months writing lines of code without writing a single piece of content, only to find that there was no audience to showcase my product. And worse, no one cared about it.
Long story short…those products are now buried in my virtual backyard.
Like the quote above, these false starts are the lessons that haunt me. They don’t keep me up at night, instead, they are reminders whenever I attempt something new. They are the voice that creeps into my mind telling me: don’t forget why we’re in the grave (sorry, a bit morbid).
TradeCruncher: “Did you stop and ask why someone wouldn’t use your product”
Scratch your own itch they say. Build it and they will come they say…Turns out, it’s not that simple.
In one of my past lives, a friend and I spent over seven months hacking on a product called TradeCruncher. It was an automated trade journaling app for options traders. Easy money right? Nope.
The impressive architecture that no one experienced
The front end was a Google Sheet template that we would share with users. It came with sophisticated formula fields and custom scripts you had to approve as a GSheet add-on.
The backend had a complex serverless architecture. It was built on a cluster of AWS Lambda functions that handled everything from user account authentication, a read-only sync with Plaid’s API to pull in trades, and the backend logic to standardize those trades across brokerage accounts.
I only add these technical details to illustrate a point: we spent all of our time thinking of why someone might want to use our product. But we didn’t spend any time thinking about why someone wouldn’t. The first obvious reason is that no one knew about us. And even if they did, they had no reason to trust us – all they would see is a website and a CTA.
No story, no connection, no sale.
The issue with focusing on features and not on your customers
The trap we fell into was believing we knew what users wanted because we were the customers. Wrong.
This startup taught me that experiencing the problem yourself is not a substitute for doing customer discovery. Moreover, that “being the customer” is not a marketing plan.
As you can probably imagine, when we launched we didn’t get any traction. We didn’t get clicks or upvotes on Show HN, we got banned from a subreddit, and a few users tried signed up but didn’t upgrade.
Our main feature, the one we spent most of our time on, was the biggest roadblock for these users. Those who gave our product a chance didn’t want to connect their accounts to a third-party site. They simply didn’t trust us.
I remember telling myself my next go I would build attention around content before I built a product. So that’s what I did.
The lesson here: Value starts with your content, not with your product – that’s how you build trust.
QualifyIt: “Don’t stop digging into the core problem, it’s the only way to learn if you truly care about it”
I’ve found the best marketers empathize with their customers. You don’t need to be the end customer yourself, you simply have to care about their pain.
After TradeCruncher, I launched a product called QualifyIt. It was a tool for tech sales reps that helped them outbound by prioritizing prospects based on recent news.
The value-prop was simple: know who to email and personalize your outreach. Again, the MVP was a Google Sheet. But the best part was I got three paying customers before I built a fully functioning product. Here’s how.
Going all in on distribution first
It all started with an article and a Reddit thread. I wrote about my experience working with Sales leaders at my past job. I told my story, described the challenges I saw, and briefly mentioned a solution.
After getting three paying customers and a handful of prospect calls, I doubled down on distribution.
My second lever was cold outreach. I didn’t want to spend hundreds of dollars on an email service like Outreach – so I manually sent 500 to 1,000 emails in a week. I created a Python script that would auto-generated Google Sheets with a template of leads and attached it to my emails. Scrappy!
I thought I was on to something until I hit a virtual wall.
The shortcomings of going too wide
The pitfall I fell into was not focusing on a niche. By going too wide too early, you confuse activity for signal. What’s worse is that you don’t dive deep enough into a core problem for one persona, and you don’t end up building empathy around that space.
Your message becomes generic. And your value-prop remains surface level. (*cough* *cough* – foreshadowing.)
Looking back, I thought the news finder was the value-add, but what sales reps really cared about was booking more calls – and one layer deeper, they really cared about hitting quota. I was just selling a widget. It wasn’t a painkiller or a game changer.
After several weeks of no progress, I lost interest in QualifyIt – another sign I wasn’t invested in the problem space. So I stopped working on it altogether. I was left in limbo until I had a brilliant idea, at least it was brilliant in theory.
The lesson here: Lead with your story, not with your solution – it helps to attract your customers early.
The ups and downs of running SaaS Weekly
A Reddit acquisition
After QualifyIt, I was looking for a new idea to tinker on. During my soul-searching journey, I came across a Reddit thread of someone trying to sell his newsletter. The thread was a few months old, and there were no takers. So I DM’d the author and told him I was interested.
The original version of the SaaS Weekly site had a simple layout. It was a paginated feed of prior curated articles and a summary. The site was started back in 2019 and the newsletter had about 750 subscribers.
A few things stood out to me from the start:
- The content was about a space I’m knowledgeable in, interested in, and currently work in (I was working at a growth equity firm at the time, investing in vertical B2B SaaS space)
- The purchase price was cheap, so the risk profile was low
- Lastly, I was fixated on the idea of building an audience base before building a product
However, buying a newsletter wasn’t exactly the “startup” I had in mind, and I had no ambitions to run a media property. Nonetheless, I put together an investment thesis for myself, outlining what I could do with the newsletter if I bought it.
I was eager to just try something new. I presented an offer and after a few back-and-forth negotiations, we landed on about $1 per subscriber.
While the acquisition was a great step forward, my ambition for growth skewed my vision. I was more excited about amassing an audience after my failed attempts – so much so, that I failed to realize I had little belief in the publication itself.
The pitfalls of my beliefs: “Your conviction must match your vision”
My ambition hinged on this one thought: building an audience before a product is a cheat code to success. While this statement is true in some regards, it’s an oversimplistic view of the whole distribution-first mindset.
Distribution over product sounds simple in theory: just promote content and capture people’s attention. But in reality, it’s still really hard. Building an audience is a grind in itself. It’s a slow process with little reward in the beginning.
The newsletter graveyard is filled with publications that ended at around 100 or so subs. Moreover, it took years for creators like Kyle Poyar and Lenny Rachitsky to build a critical mass of followers. It was their passion for the content and topic that kept them going for so long.
I’m sure that by knowing who they are writing for, the value they were providing, and the vision for their content formed the foundation for their continued conviction.
For me, I was only obsessed with growth. As a result, I realized too late that I didn’t have a clear direction. THE WHY was missing.
Failing fast is typically better than hanging on
Looking back at my past lives, the best part of my first two ventures was failing fast. It might have been painful in the moment, (losing money is never fun), but at least I did the thing. I killed the thing. And I moved on from the thing.
This was not the case for SaaS Weekly. My perseverance without the WHY slowly killed me. Like a death by a thousand cuts: you don’t realize you are bleeding out until it’s too late.
The first two years of running SaaS Weekly became my most recent “past life.” All the mistakes I made during that time have now become a new tally on my scoreboard.
The lesson here…
I learned that growing an audience is really, really (really) hard. I naively thought the key to its success was just consistency – showing up every day. But this fact is only partially true. The flip side is that your consistency must be met with direction and your conviction must match your vision.
What’s next for SaaS Weekly
The current vision
After a month of reflecting, I returned to the core of SaaS Weekly. From the start, I decided the newsletter wouldn’t be a journalist column like TechCrunch or The Information. The publication doesn’t break stories and I don’t run a newsroom.
More specifically: I’m not in the business of bringing you news, I’m in the business of guiding your growth. And this obsessive focus has set the direction.
The vision for SaaS Weekly is simple: be the go-to content hub to enable your next growth strategy.
Whether you’re a SaaS founder finding your stride to $1M in ARR or you’re a GTM leader building pipeline for a growth-stage startup, this newsletter is for you!
But hey – aren’t there a ton of GTM newsletters out there? What makes you different?
Positioning the publication
You’re right. There’s a lot of content out there. Some are good, others are bad, but very few of them actually help us make a decision.
Plus, there are a lot of “go-to resources” on how to launch your startup (e.g., YC School), but the guides on growing your startup are scattered. Everyone has opinions and not all content is helpful to you.
So instead, SaaS Weekly is the curator to help you navigate your growth journey and find the most impactful content for your context.
- It’s where you go to be inspired
- It’s where you go to find direction
- It’s where you go to discover your next growth strategy
At the end of the day, I’m building something I wish existed.
As an investor – I wish I had a resource I could share with founders or GTM leads to help refine their growth strategy. Something that could present a collection of perspectives from industry leaders that would influence their decision.
As an operator – I wish I had a resource I could refer back to when I’m designing my next marketing campaign. Something that could give me ideas on how to position my messaging or what channels to use.
As a founder – I wish I had a guide to present me with new resources and ideas consistently. Something that summarized articles I could store for later.
But more importantly, I’m building something other people have asked for. And I’m sharing the process with you.
Your journey with SaaS Weekly
As a reader of the newsletter, this is your journey too.
You can help shape what you get out of the publication.
Let me know what resources you would find valuable, and I’ll curate them for you.
The lesson here: If you read this far, then you might as well subscribe (you won’t regret it).
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