Does anyone remember my post a few weeks back where I almost invested in Anthropic at a $4B valuation? The $1M minimum could have turned into $200M+. I felt so shit after reading the comments as people reminded how dumb I was for missing out.

My Wife Called It

My wife had talked me out of investing. One of the reasons was because it was an SPV and she thought those are dodgy af.

Well, Anthropic just declared any transfer of shares to an SPV void under their transfer restrictions.

Worthless Paper

All these buyers on secondary markets like Forge or Hiive now hold worthless paper.

OpenAI faced similar issues in August 2025 and warned about "scams"... but Anthropic is the first to actually VOID existing transfers.

Market Disaster

This is a disaster for the entire private market secondary ecosystem. Anthropic's invalidation of these SPVs is going to trigger widespread market disruption and lawsuits.

Family Offices, Venture Funds and Employees are on the hook for billions of dollars now. When you're considering where to find the best AI investments, this is exactly the kind of risk you need to watch for.

Also, doesn't this technically mean that ANY company could do this now?

Key Takeaways

The secondary market for private company shares just got a lot riskier. SPV structures that seemed like a smart way to access hot deals can now be voided at a company's discretion. And when you're dealing with financial decisions of this magnitude, the consequences are brutal.

Sometimes the investment you don't make is the best one. My wife's skepticism about SPVs saved us from what could have been a catastrophic loss.

If you're investing in private markets, verify those transfer restrictions before you wire any money.

Breaking Free

The only time I could disconnect was after I sold my company and tried to retire for a few years. Otherwise, I've been addicted to the dopamine hit of social media and the adrenaline of reading an email that could ruin my night, for most of my life.

Recently, though, it's become a habit I cherish.

The Shift

I'm using the remote-control feature in Claude Code which allows me to code from my phone. I'm not wasting as much time on social media anymore.

My brain is working hard and I fall asleep sooner. I dream about engineering all night long and feel so much sharper.

Setup Guide

For those of you who are curious how to set this up:

Type in "claude --remote-control" in terminal BEFORE you start the session. This sets up a permanent server. You can then control from the Claude app.

It's not the same if you type "remote-control" within the Claude Code session (too many problems).

The Tradeoff

I know there are health issues with staring at a phone before you sleep but the tradeoff is worth it for me at this time in my life when I'm trying to grow this new startup.

Final Thoughts

Screen time before bed doesn't have to be a guilt trip. When you redirect that time toward building something meaningful, it can become one of your most valuable habits.

The key is finding ways to make your existing behaviors work for you rather than against you. If you're already reaching for your phone anyway, you might as well turn a bad habit into a productive one.

Try setting up Claude Code's remote-control feature and see if it changes your nighttime routine too.

The Conversation

Her: "So you make $1M every single year?"

Me: "Well… no… we should make it based on how we calculated revenue last month"

Her: "But you said it was annual recurring revenue. How do you actually make money?"

Me: "Our customers pay upfront for a quarter and then we multiply that by 4"

Her: "So you don't really have any recurring revenue if they can cancel after the quarter ends"

She's Right

So I guess she's right. Blazel has no recurring revenue based on the strict definition of what ARR means.

She would be absolutely mortified with how some Founders are calculating their ARR. This kind of financial blindness is more common than you'd think.

The Takeaway

Sometimes the simplest questions expose the biggest gaps in how we think about our businesses. If your metrics can't survive a conversation with someone who knows nothing about tech, maybe it's time to rethink how you're measuring success.

Honest accounting isn't just good ethics. It's good business. The founders who build real, sustainable companies are the ones who face these uncomfortable truths early. That's how you become a better CEO.

Take a hard look at your own metrics and ask yourself: would they pass the mum test?

For those of you who don't know, a major thing just happened in AI.

Category Leader Disrupted

ElevenLabs was the category leader as the #1 voice AI company. You sent them text. They returned audio. They got paid for each audio generation.

They were a great example of succeeding in the AI application layer.

And then comes along Mistral, a model provider.

The Zero-Price Threat

They just released a 3B open weights model that can run on any smartphone for free.

They basically zero-priced an entire category.

We are all building application companies on top of something that is rapidly going to zero in price. This is exactly why most GenAI startups won't last in the current landscape.

The Big Question

How can we compete with that?

When model providers can release free alternatives that match your core offering, the application layer becomes increasingly vulnerable. If you're building in AI, you need to understand how to turn a bad startup situation into an exit before the market shifts beneath you.

Final Thoughts

The AI application layer is facing a harsh reality: model providers can zero-price entire categories overnight. If 99% of founders are building here, most need to rethink their competitive moat.

This isn't about pessimism. It's about awareness. The landscape is shifting fast, and what worked yesterday might not work tomorrow.

Consider how your startup can differentiate beyond the model layer before the next disruption hits.

The language of AI is so abstract it's now written in plain ol' English. So why are you letting your AI Engineers write instructions? Do you think they have a passion for writing prose?

I bet they're just letting Claude Code run wild anyway.

Garbage in. Garbage out.

The Problem

Poorly written instructions create ambiguity. The agents misinterpret the task, pull the wrong data, call incorrect tools, and trigger unintended workflows.

An AI agent stack is dozens of instruction layers, almost all written in English:

• CLAUDE.md defines the agent's identity, priorities, and rules.
• System prompts control tone, format, and interaction style.
• SKILL.md files describe what the agent can do and when to use those skills.
• Tool descriptions explain what each tool does and when to use it.
• Workflow instructions define how tasks are broken down and routed.
• Sub-agent definitions specify the role and scope of specialized agents.
• Retrieval instructions guide how the agent searches knowledge bases.
• Memory guidelines define what the agent should remember or summarize.
• Examples are sample inputs and outputs that teach the agent how to behave.
• Evaluation prompts test scenarios that verify expected behavior.

The quality of the English directly determines how your agent interprets tasks, selects tools, and behaves in real situations.

Writers Win

A writer who knows how to structure a clear argument, write an instruction with no room for misinterpretation, and catch the moment a paragraph contradicts itself three paragraphs later is invaluable.

They will become some of the most in-demand people in building AI systems. And if you're serious about building an AI startup, you'll want these people on your team early.

This new role will be called a 'Content Engineer'.

The Takeaway

Content writers aren't going anywhere. In fact, they're becoming more essential than ever. The entire AI stack runs on English instructions, and the people who can write clear, unambiguous prose will shape how these systems behave.

If you're a writer wondering where AI fits into your future, here's your answer: you're not being replaced. You're being promoted. The skills you've built around clarity, structure, and precision are exactly what AI systems need to function properly.

Start thinking of yourself as a Content Engineer. Understanding how to become a better leader in this space means recognizing that writing is now a technical skill.

So why do I feel so sh*t?

It's a rite of passage on LinkedIn to post this milestone. Yet, I don't feel like celebrating.

Comparison Trap

Every week, another AI startup hits $10M ARR in months. Why aren't we growing at that pace?

We raised lots of VC so we can hire amazing talent and become the best at helping execs publish B2B content on LinkedIn (to start with).

But now we have to worry about metrics like burn rate and out of cash date.

If our growth isn't exponential, we will struggle to raise our next round and... basically die.

Existential Threats

Then there's the constant worry that OpenAI, Anthropic or Google will creep into the application and marketing services layer and crush us.

Every time we discover an amazing way to work with Claude or automate an internal workflow, some YouTuber gives it away for free weeks later.

It is so hard to build competitive moats when the ground keeps shifting like this every month. This pace of innovation is dizzying. It's one of the hardest challenges AI founders face right now.

Fleeting Loyalty

Customers are also not loyal in this AI age.

They have experimental AI budgets and will 'test' multiple competitors at once.

This $1M ARR could vanish as quickly as it came.

The Silence

No one talks about this sh*t in public because there's zero upside in doing so.

Am I the only Founder feeling this way?

Here's the reality: hitting milestones doesn't mean the anxiety goes away. The comparison to faster-growing startups, the threat of big tech crushing you, the constant innovation making your moats obsolete, and customers who aren't loyal. These are the real struggles behind the celebration posts.

If you're a founder feeling the same pressure, know that you're not alone. The wins don't always feel like wins when the ground keeps shifting.

We were in a fancy office fresh with VC funding and ready to do exactly what startups are supposed to do… hustle and get creative.

What we did and the results

We “sponsored” the food

We offered free linkedin help

Sixty five people attended an exclusive webinar

Our ICP is B2B Founders & Execs who can be found all over these co-working spaces. The perfect place to launch our plan.

Apparently, the legal team thinks Caitlin O. Bigelow’s marketing activities violated their ‘code of conduct’.

I’m cashing in some karma points. I need my real estate and founder connections to pay off or we’re screwed.

We have 5 days to vacate and are looking for a temporary place for our team to work in the Bay Area (even just one day / week) whilst we scramble to find a permanent office.

Tag a founder who might have extra space. We need help ASAP.

In summary, our startup is facing eviction due to some guerilla marketing tactics. We need a temporary office space in the Bay Area while we search for a permanent solution.

If you know of any founders who have extra space, please reach out. We're in a tight spot and any help would be greatly appreciated. Maybe it is time to learn how to become a better CEO.

Tag a founder who might have extra space. We need help ASAP.

As a father to a newborn, I am a strong advocate for 9am-5pm. Plus 10pm-2am. And also 4am-6am.

Zero Balance

No seriously, there is zero balance if you're running an AI startup right now. If you have kids, you still have to put in the hours.

I'm literally running investor calls with a burp cloth over my shoulder and prompting Claude Code in between diaper changes. I'm operating on 3-hour sleep cycles while a 7-pound human dictates my entire schedule.

Shared Pain

To anyone who is a startup founder and has young kids, I feel your pain. We have no choice as our startup is our baby too. The truth is, work-life balance is broken for founders in this stage.

I don't even have time to finish this post.

Gotta run. Someone needs changing and it's not the cap table.

Final Thoughts

Running an AI startup while raising a newborn means accepting that balance doesn't exist right now. You work the hours you can, whenever you can, because your startup is your baby too.

If you're a founder with young kids, know that you're not alone in this. The grind is real, and so is the exhaustion. If you're figuring out how to turn a bad startup into a successful exit, the path forward requires exactly this kind of relentless dedication.

Keep pushing. Your kids will understand one day.

There are many moments in my life that have made me question reality: The Matrix Movie, The Sims, VR, Deepfakes and now Project Genie.

On-Demand Reality

This is the first time I've seen a system behave the way a simulated universe would have to behave for it to be computationally feasible.

Instead of prebuilding a world and letting you walk around inside it, Project Genie renders reality on demand as you move, look, and act.

Two people can use the same underlying model and get completely different worlds, purely based on their prompts and actions. It's similar to how you and I inhabit this same physical world but we live in very different subjective realities.

Scaling Infrastructure

For a simulated reality to work at scale, we would need an unbelievable amount of power and infrastructure but that's exactly what's happening.

There is even serious talk about off-planet compute, where you have essentially unlimited solar energy and no NIMBYs to block it. Many companies are already turning ambitious ideas into massive enterprises, and the infrastructure for simulation-scale computing is no different.

Reality Stack

If you fast-forward a few decades, I think we end up with something that looks uncomfortably close to a full "reality stack":

• Compact world models at the bottom
• Crazy amounts of compute and power in the middle
• Human (or Animal) consciousness sitting on top of it all, none the wiser

Existential Questions

There are already billions of us walking around convinced this is "real life," yet we can't explain why anything exists, why consciousness feels the way it does, or where we go when we die.

In that context, Project Genie feels like a small but very real hint that the thing we call reality might just be someone else's well-engineered simulation. These are the kinds of questions that shape how we think as leaders and builders.

Final Thoughts

Project Genie represents a shift in how we think about simulated worlds. On-demand rendering, subjective realities, and massive infrastructure investments all point toward a future where the line between simulation and reality becomes increasingly blurred.

Whether or not we're living in a simulation today, the technology to create one is advancing rapidly. The implications for AI, consciousness, and our understanding of existence are profound.

What do you think? Does Project Genie change how you see reality?

Expectations Gap

Advisors think they'll meet a few times per year and earn free equity for their advice. The founders, on the other hand, have an unreasonable expectation for hands-on execution, unlimited responsiveness, and tons of intros.

The founder ultimately gets annoyed but doesn't want to fire the advisor as they'll burn the relationship so the advisor keeps on vesting.

Serial Advisors

This is so common that there are literally serial advisors who make a career out of this. They stack multiple roles over the years (like 20-50) anticipating a power law outcome.

Better Alternative

Most tech advisory roles should actually be consulting roles. This means a clear scope, short duration, and either an hourly or fixed fee (doesn't matter if paid by cash or equity).

When Advisors Work

There are only a few rare instances where bringing on an advisor makes sense otherwise it's expensive and scopeless:

• You want to hire them full-time in the near term
• You want them to join as an independent board member
• You need credibility in your industry (serial advisors love this)
• You are giving extra upside to an investor as part of a fundraising negotiation (sneaky)

CEO Advice

I also believe tech CEOs should never advise other companies. If you truly want to help, then join as an independent board member.

Understanding how to become a better CEO means knowing where your time creates the most value.

Conclusion

The lesson here is simple: if you're a founder, think twice before giving away equity for advice. If you're considering an advisory role, understand the real expectations. Most of the time, a consulting arrangement with clear scope and deliverables serves everyone better than an open-ended equity deal.

Founders who are building their next company should learn from others who turned challenging situations into major exits. The right structure for every relationship matters.

Before you bring on your next advisor, ask yourself: would a consulting agreement accomplish the same thing?

I am against hiring Product Managers in startups. Product should be the responsibility of the Founders, preferably the CEO.

At Vungle, I made this mistake and thought hiring PMs would magically fix our problems. I witnessed even more issues instead.

What Went Wrong

When we brought on Product Managers, things got worse:

• Sales team taking over our roadmap
• We shipped too many useless features
• Endless meetings and documents

A PM is going to be pulled in so many directions. They will say YES quickly and ship tactical features to show quick wins inside the org.

No Strategic Thinking

There is zero strategic thinking. There is no incentive to build long-term competitive moats.

Only the Founder or CEO can do this. They have the full context. They can say NO to most things. Learning how to become a better CEO means owning this responsibility yourself.

PMs Are Obsolete

In this day and age, you don't even need PMs.

Why bother with all that documentation when you can get it generated in seconds via an LLM? You can literally vibe code a full-stack MVP in hours without much technical knowledge.

This is one of the things I'm doing differently in my new AI startup.

Final Thoughts

Product is not something you should ever outsource. It belongs with the founders who have the vision, context, and authority to make the hard calls.

When you hand product responsibility to someone else, you lose the ability to say no. You lose strategic focus. You end up chasing quick wins instead of building something that lasts.

If you're a startup founder, own your product. It's too important to delegate.

Now, I know that sounds cocky as hell but I got absolutely screwed in my pre-seed as I didn't know how to read a term sheet.

VC Games

VCs can be nasty. They can sneak in all these extra terms. Meanwhile, you get distracted focused on headline terms and neglect the small print.

So this time, I was going to do things my way.

My Approach

I wrote the term sheet and modified all the small terms to be exactly what I want and then let the VCs set the price.

My justification was simple: "We have so much interest, I need to compare Apples to Apples."

Unexpected Results

The crazy thing is, sending that TS to all these VCs was such an unexpected thing to do.

They sensed there must be competition and it turned into an all-out bidding war.

First TS came in at $7M on $30M. Within a few weeks, we had 7 VCs fighting. We ultimately went with the highest offer: $17M on $100M.

I did not feel we deserved such a high valuation but that's what running a good process does. This experience, along with how Jack and I turned a bad startup into a $780M exit, taught me that fundraising strategy matters just as much as the product itself.

The Takeaway

If we all raise our early rounds on YC SAFEs, why can't we also apply the same logic to late stage funding rounds?

Understanding term sheets is part of addressing founders financial blindness that costs so many startups in the long run.

Conclusion

Running a tight fundraising process can dramatically change your outcomes. By controlling the terms and creating real competition, you put yourself in the driver's seat.

Don't let VCs dictate every aspect of the deal. When you have leverage, use it wisely.

If you're lucky enough to have multiple VCs interested, this is something you could try.

One day, you will hopefully go through a process and then you can thank me.

The Avalanche of Requests Is Coming

When that time comes, you will get endless requests for things like:

• IP assignments
• Every single customer contract
• Board consents
• Open-source licenses
• And much more

The list goes on and on. It can feel overwhelming, but it doesn’t have to be.

Don’t Pay Attorneys to Shuffle Papers

You do not want to be paying an expensive attorney to shuffle papers. But you might just do that because you will be way too busy. Most of this data should already exist but it’s usually buried somewhere in your archived mail (or an ex-employee’s folder, which is even worse).

If you do this well, you can just send a link to the data room and then go on vacation in the middle of the process (just kidding). But seriously, the other side will be impressed. You will inspire trust which is what gets deals closed.

How to Actually Make This Happen

If you’re large enough, assign it to an admin or ops person. But they won’t do it unless you demand it’s done properly as all humans are lazy.

If you can’t afford that, just make it a personal ritual like having ‘inbox-zero’ or sending out investor updates so it’s just something you allocate time to every now and then.

Trust me, there is zero downside to being organized.

The Real Reason Fundraising Feels So Tiring

Yes, it doesn’t come naturally to many founders but that’s also why these same people lament at how tiring the process can be.

The truth? It’s tiring because you’re a disorganized train-wreck.

Being organized from day one makes fundraising and acquisition processes exponentially smoother.

Conclusion

Your future self will thank you when you’re not scrambling through old emails at midnight trying to find that critical contract from two years ago.

Start building your data room today. Make it a habit. Make it part of your company culture. The payoff when you need it most will be worth every minute you invest now.

Artificial intelligence is helping them break out three times a year, year over year, but venture capitalists do not care.

The Problem

The current environment favors new startups going from a standing start of zero dollars to one million dollars plus annual recurring revenue in a short time, like less than six months.

Startups with a few years of slow history look tainted.

Like they are from the old software-as-a-service era, whereas new must mean they are artificial intelligence native.

The Narrative

“But we have embraced artificial intelligence and are now growing fast.”

This story will not resonate with investors.

Yes, it is a mistake investors are making, but it is the reality right now.

Hidden Value

Existing startups with new momentum have solid foundations.

They have a proven team that has worked together longer and understands the industry so much better than a new company.

In my opinion, these are amazing companies.

The older the company, the less risky it is.

The best risk-adjusted returns will be found in companies pivoting to artificial intelligence.

My Advice

If you are a company in this situation, I think one or two more years of growth will wipe the slate clean if you want to raise funding.

Your growth will look even more exponential over time if you choose to do your Series A.

In the meantime, I am advising my portfolio companies in this situation to focus on profitability.

Conclusion

Venture capitalists may be overlooking the best opportunities by favoring brand-new artificial intelligence startups over established companies successfully pivoting to artificial intelligence.

Patient founders who focus on profitability and sustained growth will ultimately be rewarded with better valuations and less risk.

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I weighed 170 pounds earlier this year and was in the best shape of my life.

A year ago, I was competing in martial arts and benching 225 pounds.

Then I decided to jump back into the game and build my new stealth AI startup.

The Fitness Falloff

I went from hitting the gym 5 times a week to barely 1 time a week.

Working out keeps getting pushed to weekends.

Before, I would go on random walks or hikes during the day.

Now I am sitting behind a desk all the time.

Startup Life Reality

My family is tired of hearing about my new startup 24/7, but that is all I can talk about.

I still try to order healthy when I have business lunches or dinners, but literally everything on the menu is loaded with calories and sugar.

This was not as tiring when I did my last startup in my 20s, but in my late 30s, I seem to be really feeling it fast.

The VC Perspective

When I was a VC, I used to tell founders in my portfolio to focus on work-life balance, as I eventually suffered burnout.

They would look at me with blank stares.

Of course, I felt like some wise sage having crossed another dimension.

In truth, I was just disconnected from reality as I became a VC, which is nowhere near as stressful and tiring.

Conclusion

I have since concluded that it is simply not possible to maintain work-life balance when you are running an AI startup, especially in this era.

The physical and mental toll is something founders understand but rarely talk about openly.

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As an experienced investor, I have discovered this simple yet powerful indicator of a company’s execution capabilities.

The Bug Test

Early-stage websites typically have their share of minor issues.

These range from broken links to typos to malfunctioning signup forms.

The bugs themselves are not the real concern. It is the response time that matters.

Red Flags

Some founders completely outsource their website management to remote agencies.

They find themselves unable to make even simple changes, like updating a headline, without submitting a ticket.

These founders often wait days or weeks for basic fixes.

When I observe this pattern, it immediately signals a lack of essential marketing and sales DNA needed for competitive success.

Speed Champions

The most promising founders I encounter resolve bugs within minutes to hours.

This swift responsiveness is not limited to website maintenance. It extends across all aspects of their business:

• Product shipping velocity
• Customer feedback implementation
• Achievement of product-market fit

Competitive Edge

For startups, execution speed is often their only true advantage.

Your website serves as a critical part of your sales funnel.

The fundamental question becomes clear:

If you cannot fix your own website quickly, how can you possibly compete against someone who can?

Conclusion

Website maintenance speed serves as a powerful indicator of a startup’s overall execution capabilities and future success potential. The ability to quickly address issues reflects a company’s agility, technical competence, and customer focus.

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The Coffee Shop Challenge

Working from coffee shops was becoming increasingly unsustainable for our team of three.

Every day brought the same frustrations:

• Constantly searching for parking
• Spending time ordering drinks
• Guarding tables
• Moving between coffee shops and hotel lobbies
• Dealing with unreliable WiFi

Why An Office Matters

As a startup in the crucial 0-1 phase, we need to be together in person five days a week.

Productivity was suffering without a dedicated space.

The nomadic lifestyle was killing our efficiency.

Our New Setup

Now we have everything we need:

• A stable workplace
• Multiple screens
• Reliable WiFi
• Dedicated meeting space
• No more daily relocations

Looking Forward

While we are maintaining stealth mode about our actual location, this move represents a crucial milestone for our AI startup.

We finally have the foundation we need to focus entirely on building our product.

Conclusion

Sometimes the simplest solutions, like having a dedicated office space, can make the biggest difference in a startup’s early days.

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I’m often shocked to discover founders who have no clue about their monthly burn rate. When I ask, “What’s your monthly burn?” I sometimes get blank stares or a dismissive, “Our accountant hasn’t closed the books yet.”

I don’t understand how you can raise (and spend) millions of dollars with this attitude.

Daily Vigilance

When I founded and ran Vungle, I would open our bank balance every single day and night. I had a spreadsheet and would evaluate the impact of each expense on our runway and net burn.

I caught some ridiculous expenses and even uncovered someone embezzling.

This financial discipline took us to $60M+ EBITDA while competitors were going bankrupt.

Calculated Burn

We had months of insane burn, especially in the beginning but I knew exactly what was happening and it was calculated.

So I’m not against high burn at all. In fact, I’m planning to ramp up burn significantly in my new startup too.

I just cannot grasp this reality. It’s like playing a 1st person shooter game with no care for remaining ammo and health. You just hit that trigger and keep firing until you get shot.

Sloppy Spending

In 2021, you could get away with being this sloppy as VCs didn’t push much on financials.

I most often see this behavior when Founders raise money without a board (often convertible notes).

Also, if you think I’m kidding, go ask some CFOs, Accountants, professional CEOs or VCs just how common this is!

Conclusion

Ignoring your burn rate is like playing a video game without watching your health or ammo. You need to be aware of your spending to stay alive. It’s especially important for founders to maintain financial discipline, catch unnecessary expenses, and plan for calculated burn.

If you are a founder, make sure you know your monthly burn rate. Open your bank balance. Create a spreadsheet. Stay on top of your finances. Ask CFOs, accountants or VCs to get a deeper understanding on how common this is.

Don’t let financial ignorance sink your startup!

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But what if this common courtesy is actually sabotaging your most important connections?

Here’s a simple email hack that can make the difference between a response and radio silence when it comes to VIP introductions.

The Problem

Most people default to the polite approach when handling introductions.

You send a quick “Thanks – Moving you to BCC to spare your inbox” and remove the person who made the intro. This seems considerate, but it creates a major problem: you’re completely stuck if the recipient doesn’t respond.

There’s no backup plan, no way to follow up, and no additional pressure for the recipient to engage.

The Solution

For important introductions like potential investors or customers, keep the original person CC’d throughout the conversation. Don’t move them to BCC, even if it feels less polite.

This simple change gives you multiple advantages and significantly increases your chances of getting a response.

The Strategy

Here’s exactly how to handle it. When you receive an important introduction, reach out to the intro-maker privately with a message like:

“I didn’t put you on BCC as this is a really important intro – just in case they don’t respond, you might be able to nudge them for me.”

This transparent approach serves multiple purposes. It shows you value the introduction, keeps your options open, and maintains accountability.

Why It Works

There’s additional pressure to respond when the original intro-maker is still CC’d on the conversation.

Recipients know that their response (or lack thereof) is visible to the person who vouched for the connection. This social dynamic works in your favor and increases response rates significantly.

The intro-maker also remains available to provide context or encouragement if needed.

Conclusion

Small details like this matter tremendously when you’re dealing with high leverage introductions. The difference between BCC and CC might seem minor, but it can determine whether your most important connections actually materialize. Don’t let misplaced politeness cost you valuable opportunities.

Remember, the person making the introduction wants to see it succeed. By keeping them in the loop, you’re not being rude – you’re being strategic about maximizing the value of their effort.

Next time you receive a VIP introduction, skip the BCC and watch your response rates improve.

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Hybrid Revenue

The best AI startups have adopted a hybrid model consisting of a free tier or base subscription and then a usage or credits based pricing model on top.

The sticky recurring revenue that SaaS companies charge caps the maximum you can earn per user. Charging on transactions or usage allows revenue to scale exponentially with usage and lets you extract max value from the heavy users.

Self Serve

Top AI startups are purely self serve with no human involved as that adds friction with onboarding customers. You get immediate value, within minutes.

You hit the landing page, sign up and are using the product straight away. The teams are obsessed with optimizing this conversion funnel. The ACV is very low too ($10 to $50 per month) so conversion rates are very high.

There may be an “Enterprise tier” where a human is involved but for the most part, self-serve is the first entry point.

Paid Media

Most of these growth stories are actually fueled by massive ad budgets. Google and Meta are minting money from AI startups buying ads to manufacture traction.

I know a lot about this as my last company (Vungle) made so much money from VC-backed unicorns spending money on my platform during the mobile app boom.

The Formula

When you strip it down, the AI unicorn playbook looks a lot like this:

• Hook users with a self-serve product
• Monetize them with a hybrid subscription + usage model
• Accelerate growth with paid media

Conclusion

This proven formula shows that AI unicorn success isn’t just about having great technology. It’s about combining the right pricing model, user experience, and growth strategy to maximize both user acquisition and revenue per customer.

Now go raise a bunch of money and copy this playbook for your own AI startup!

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We invested in a founder who threatened us with legal action simply because we asked for quarterly financials.

Here’s the full story.

Standard Practice

From my experience running a VC fund previously, I saw that most founders were great at sending quarterly updates.

This isn’t an unusual request. It’s actually standard practice in the investment world.

Legal Obligations

Many VC funds NEED these updates because we have a legal obligation to our own investors (Fund LPs) to provide an estimated portfolio value.

Without any news from a founder, we have to assume the worst and mark a company down to zero, which is bad for everyone involved.

The Revelation

After many investors pushed for transparency, the founder let us all know that we invested on a YC SAFE, which means we have ZERO information rights.

Unfortunately, it turns out he is correct about this.

Escalation

Things got worse when he privately messaged us and other investors, stating that if we emailed the investor list again, he would take legal action for tortious interference.

Current Situation

No one has emailed the investor list in 6 months. I have since started another company but am still bothered by this situation when I think about it.

Your Input

This experience highlights the potential pitfalls of certain investment structures and the importance of understanding your rights as an investor before committing funds. The YC SAFE structure, while founder-friendly, can leave investors in a difficult position when it comes to basic transparency and communication.

If you were in my shoes, what would you do? This situation serves as a cautionary tale about the importance of reviewing investment terms carefully and understanding the implications of different funding structures.

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According to Zain Jaffer, founder and CEO of a Stealth Startup, ‘Founders must either focus on profitability or commit fully to scaling past $3M ARR trying to do both will fail in today’s VC market.’

In the present Series A landscape, startups are required to either bootstrap with a focus on disciplined, profitable growth or engage in rapid scaling to achieve $0–$3M+ ARR with significant burn rates.
Attempting to navigate both approaches simultaneously poses the risk of scarce investment and reduced momentum.

Click here to view the full post.

This insight reflects the reality that successful startups must embrace focused execution rather than trying to satisfy multiple conflicting approaches.

As highlighted in Rise & Recognise’s feature, choose your path and commit fully to making it work.

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This represents a major change from just a few years ago, when you only needed to reach $0 to $1M ARR in your first year to secure the next funding round. Today’s reality is much more demanding.

Higher Stakes

In today’s market, VCs at the Series A stage have become momentum-chasers. They’re piling money into relatively few AI deals where the minimum bar has jumped to $0 to $3M+ ARR.

This shift has major implications for how founders should be managing their cash burn and overall strategy.

Two Paths

There are only two legitimate ways to run a VC-backed company in today’s environment:

• Bootstrapped Approach: don’t worry about aggressive ARR growth. Instead, have discipline and focus on profitability or maintaining a low burn multiple. Grow sustainably over time without the pressure of massive funding rounds.
• Blitzscaling Strategy: commit fully to reaching $0 to $3M+ ARR by burning lots of money to accelerate growth. If you pursue this path, you also need to raise a large enough round to sustain the high burn rate.

Avoid This

The biggest mistake founders make is trying to play both sides. This means maintaining moderate burn while only being on pace to hit $0 to $1M or $0 to $2M ARR. This approach leaves you in a dangerous situation where you need more VC funding, which is extremely tough to pull off in the current market.

Conclusion

Either path can yield great outcomes for your startup. However, straddling both strategies at the same time is too risky and often leads to failure.

The key is making a clear choice and fully committing to your chosen strategy rather than getting stuck in the middle ground that satisfies neither investors nor sustainable growth metrics.

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This is the story of how we achieved $100K ARR in just 6 weeks while deliberately staying out of the public eye.

The numbers speak for themselves, but the strategy behind them might surprise you.

Lightning Growth

About 2 weeks ago, our startup hit $50K ARR. Then, we just broke through $100K ARR in our first 6 weeks.

I’m going to stay in stealth for a while longer as I don’t see any upside to launching publicly yet. We are onboarding so many new customers every week so focusing on anything else right now is a distraction, except keeping them happy.

Real Challenges

Success doesn’t come without its bumps. I do fear I’ve taken on more than I can handle. I lost my first design partner just DAYS after we celebrated $50K ARR.

Given the bad luck last time, we’ll probably lose another customer immediately after posting this. It’s the reality of rapid growth that not everything goes smoothly, even when the numbers look great.

AI Advantage

One thing I’m surprised about is the ability to execute so fast thanks to AI tools. It’s unlike anything I’ve witnessed before as a former VC and as a repeat founder.

For context, my last startup, Vungle burned $200K+ per month in its first year and that’s before we even made any revenue. In this new startup, burn is modest but efficiency is 10X and revenue is immediate.

We’ve built more in 2 months with a tiny team than the entire first year at Vungle with a huge team. The difference is staggering when you have the right tools at your disposal.

Stealth Benefits

I’m also proving here that it is 100% possible and advantageous to stay in stealth and still make solid progress.

While everyone else is focused on launches and publicity, we’re focused on what matters most: customers and revenue.

Conclusion

The road to $100K ARR in 6 weeks proves that sometimes the best strategy is the quiet one.

By staying in stealth, focusing on customer satisfaction, and leveraging AI tools for maximum efficiency, rapid growth is possible without the typical startup fanfare.

The combination of modest burn, immediate revenue, and a small but effective team creates a formula that older startup models couldn’t match.

Ready to rethink your startup strategy and focus on what really drives growth? Follow me on LinkedIn for more content like this.

Here are the 5 major changes I’m making based on what I learned from my previous experience.

Skipping Customers

In my prior startup, I wasted time listening to potential customers.

Now, I’m skipping customer discovery entirely.

Steve Jobs and Elon Musk didn’t need to listen to customers, so why should I?

The best products come from vision, not feedback.

Investor Focus

Last time, I only cared about product-market fit. This time, it’s all about investor-founder fit.

I’ll adapt my pitch to whatever each VC says they invest in.

Meeting their expectations is more important than sticking to one rigid vision.

Hiring Fast

Back then, I hired slowly and carefully, taking time to find the right people.

Now, I’m hiring a Head of Growth, Chief of Staff, and “AI Evangelist” before we even launch.

Building the team early sets us up for rapid scaling.

Smart Priorities

I used to worry about churn and gross margins, but now I spend all my energy on things that actually matter:

• Finding a cool .ai domain
• Logo design
• Filing patents
• Looking for fancy office space

These elements build credibility and brand value from day one.

Stealth Strategy

I thought about nonsense like go-to-market strategy and distribution channels.

Now, the best strategy is staying in stealth forever.

Nothing builds hype like saying nothing. Mystery creates demand.

Conclusion

These five strategic changes represent a complete shift in how I approach building a startup. Instead of focusing on traditional metrics and customer validation, I’m prioritizing investor relationships, team building, and brand positioning from the start.

Here’s a summary of the 5 major changes I’m making in my new AI startup:

• Skipping customer discovery completely instead of wasting time on feedback
• Focusing on investor-founder fit rather than just product-market fit
• Hiring key executives before launch instead of careful, slow hiring
• Prioritizing brand elements like domains, logos, and office space over metrics
• Staying in stealth mode forever to build hype through mystery

If I had done these 5 things differently the first time around, I’m 100% sure I wouldn’t be where I am today.

Sometimes success means completely flipping your approach and doing the opposite of conventional wisdom.

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This is the story of how we built a “services as software” startup that hit $50K ARR in just 30 days by combining the best of both worlds.

Rapid Progress

A month ago, I posted about getting my first design partner at $10K ARR so things are progressing well as we now have 5 paying design partners.

The growth from one design partner to five shows the power of focused execution and a clear value proposition that resonates with the target market.

Services Software

I’m focused on a new category known as “services as software” in the marketing space and am using a combination of AI Agents plus Humans. This hybrid approach allows for the efficiency of automation while maintaining the quality and creativity that only humans can provide.

I was inspired by conversations with big company CMOs who spend millions of dollars in marketing headcount or external agencies providing this particular service and they still struggle. I figured that I could provide even better value for a fraction of the price but I’m not quite ready to work with those large companies yet.

Strategic Patience

I’ll need SOC2, case studies and a lot of patience to endure enterprise level sales cycles right now. My bias is to make revenue ASAP as a tiny startup with limited resources.

So I’m building a “wedge product” with an ICP that can move fast: B2B startups with $1M+ in funding or revenue (hence my profile banner). This allows for quicker decision making and shorter sales cycles while building the foundation for larger opportunities.

Learning Strategy

My theory is that if I can make 100 demanding SMBs happy, I’ll gain valuable knowledge which will help me later when I go after larger companies at higher price points. Each small business client becomes a testing ground for refining the service and proving the concept.

This approach builds credibility, case studies, and operational excellence before taking on the complexity of enterprise sales.

Conclusion

Hitting $50K ARR in 30 days by combining AI agents with human expertise proves that the “services as software” model has serious potential.

The strategy of starting with demanding SMBs rather than jumping straight to enterprise clients creates a foundation of knowledge and case studies that will be invaluable for future growth.

Ready to explore how AI and human talent can transform your service offerings? Follow me on LinkedIn for more content like this.

The reason is simple: too many founders are making the same mistakes, building products that lack defensibility or staying power.

Here are three common mistakes I keep seeing and what I would build instead.

Hard-Coded Prompts

Many products rely on hard-coded prompts like:

• “Take a deep breath and think step by step…”
• “Act like a helpful financial assistant who works in a bank…”

If your product’s magic depends on a specific prompt behaving a specific way, it is fragile. It will eventually break when the internal model weights change.

What to build instead: Prompt templates.

For example:

“Write a follow-up email to {{customer_name}} about {{product_feature}}”

This structure is far more stable because it is generic, reusable, and not dependent on quirks in the model’s behavior.

“Copilot for X” Wrappers

Another common pattern is the endless stream of “Copilot for X” products — wrapper apps that sit on top of a vector database to surface data.

The problem: foundational model providers are creeping into the application layer. They do not care about protecting your business or mine.

What to build instead: Agentic workflows.

Rather than sitting beside the work, sit inside the system doing the work with company-specific logic. For example:

When a finance manager submits a vendor contract, an AI agent could check if it is within budget, rewrite pricing and payment terms to match policy, attach required documents, and then send it to the first approver.

This type of workflow cannot be easily replaced by generic tools. It embeds directly into processes and creates lock-in.

Multi-Agent Reasoning Loops

You have probably seen the demos: one agent proposes a plan, another critiques it, a third rewrites it, and so on.

The issue is that, without grounding in actual results, this is just large language models arguing — or worse, hallucinating — on top of each other.

What to build instead: Self-learning agents.

A real system should track what actually happened:

• Did the email convert?
• Did the ticket close?
• Did the workflow succeed?

Then it should use those signals to refine its behavior.

For example, if the legal team repeatedly rejects certain clause structures, the agent learns the pattern, rewrites content based on who is reviewing, and adjusts over time to increase approval rates.

Conclusion

If your product is not embedded in the work, grounded in context, and learning from real outcomes, it is only one OpenAI announcement away from being replaced.

Here are the key takeaways from this article:

• Hard-coded prompts are fragile; prompt templates are more durable
• Wrappers like “Copilot for X” will fade; embedded agentic workflows create stickiness
• Multi-agent loops waste resources; self-learning agents grounded in outcomes create real value
• Defensibility in AI comes from context, integration, and continuous learning

The future belongs to startups that build systems tied to results, not gimmicks.

One of the co-founders was based overseas. The founders had only met a few times, and I could sense real tension between them. The distance and lack of alignment only made things worse.

Dysfunction at the Top

It reminded me of couples on the brink of divorce who believe having a baby will fix everything. Startup founders do the same thing. They try raising money or bringing in a new executive, hoping it will magically solve their dysfunction.

Unfortunately for me, I was that new executive.

When I looked into the accounts, I discovered money was being siphoned away. The remote co-founder was embezzling company funds.

Everything Falls Apart

When we confronted him, he locked us out of all accounts.

My boss, Jack (the local founder) turned out to be a victim too. Together, we poured every dollar of new revenue into legal fees.

But the deeper we went, the more it became clear: a lawsuit would drain us completely.

A Better Idea

Eventually, someone gave us the best advice we could have received: stop chasing the lawsuit and start building something new.

So that’s exactly what we did.

Me and Jack

Conclusion

What began as a disastrous startup experience turned into the foundation for something much bigger. Jack and I went on to build a new company together — and seven years later, we sold it for $780 million.

Here are the key takeaways from this article:

• Joining a dysfunctional team can feel like a disaster, but it can also lead to new opportunities
• Founders often try to solve deeper issues with surface fixes like fundraising or new hires
• Transparency and trust between co-founders are essential
• Sometimes the best move is to stop fighting the old battle and start building something new

What feels like a setback can be the starting point of your biggest success.

A startup announces a round and ships a product. Within weeks, five clones appear. One is cheaper. Another is open source. A third is already running ads. Suddenly, your launch becomes their lunch.

In this environment, speed doesn’t look like an advantage anymore. Without real lock-in, it’s starting to feel like a liability.

What VCs Are Seeing

From the investor side, there are clear patterns emerging:

• Most GenAI startups are wrappers on public APIs with a slick UI
• Many founders claim to be building “infrastructure,” but in reality, the product looks more like prompt templates
• Pricing trends toward zero unless there is a clear ROI story
• Frontier labs are moving into the application layer, directly threatening portfolio companies

Several VCs have admitted they are considering a pause, given how quickly things are shifting.

What Founders Are Facing

For founders, the challenges are equally stark:

• Proofs of concept are easy to land, but renewals remain a struggle
• Enterprises are curious, but security reviews and on-prem demands often kill momentum
• Competitors can offer extreme levels of customization because the underlying build is simple
• Many teams mistake early interest for genuine product-market fit

Even experienced founders are feeling the strain. Burnout is visible, and strong operators admit that every new announcement from Sam Altman or another major player reshapes the ground under their feet.

Where Real Opportunities Exist

Despite the noise, certain areas show promise:

• Products directly tied to revenue or cost savings, not vanity outputs
• Workflows that deliver end-to-end value rather than surface-level automation
• Systems that learn from customer behavior, not just respond to prompts
• Tools that integrate deeply into messy, real-world environments such as CRMs, ERPs, emails, and internal databases

The dream remains pricing on performance, though it carries risks. Covering API costs or running your own infrastructure can be expensive, even with AWS and GCP credits to soften the blow.

Most GenAI products are still flashy demonstrations — the equivalent of saying “Look what it can do.” The more durable opportunities are grounded in a different question: “Did it work?”

Rethinking Visibility

I used to believe every founder should build in public and announce frequently.

Lately, I’m questioning that approach. There are real merits to staying in stealth.

After all, do I really want to invite more competition before I even begin?

Conclusion

This market is moving at dizzying speed. For founders and investors alike, the landscape is full of excitement but also exhaustion. Amid the noise, the lesson is simple: the future belongs to products with depth, defensibility, and direct impact, not just those that look impressive in a demo.

Here are the key takeaways:

• Speed without defensibility is no longer an advantage in GenAI
• Many startups are wrappers with little moat, and pricing races to zero
• POCs come easily, but renewals and enterprise adoption remain tough
• Real opportunities lie in ROI-driven products, end-to-end workflows, and deep integrations
• Building quietly may be smarter than building loudly in today’s climate

I am still exploring ideas and 100% committed to starting another company. For now, knowing what not to build is its own form of clarity.

I currently serve on four, and I can say with confidence it has been one of the best learning experiences of my career. It changes how you see the game.

Perspective

When you’re inside the boardroom, you gain perspectives that are difficult to acquire anywhere else:

• You begin to recognize patterns faster
• You understand how VCs and independent directors think
• Corporate governance stops feeling abstract
• You see how critical decisions are made — whether in a crisis, during M&A, or in periods of hypergrowth

Commitment

The time commitment is not overwhelming.

Boards typically meet quarterly, sometimes over a dinner, and occasionally in response to an urgent matter.

As a founder, you are not expected to drive like a VC. Your role is to contribute where you can, and even that exposure sharpens your judgment.

Benefits

Simply being in the room changes how you approach your own company:

• You learn how to navigate your own board more effectively
• You earn respect from VCs by showing you understand how the process works
• You avoid the blind spots that often hurt companies
• You gain the chance to support another founder and even earn equity along the way

Conclusion

Most founders clash with their boards because they have never experienced what it looks like from the other side of the table. Don’t be that person.

Here are the key takeaways from this article:

• Serving on a board gives you rare visibility into decision-making
• The commitment is manageable but the lessons are invaluable
• It builds credibility with investors and strengthens your leadership
• Supporting another founder is both rewarding and educational

If you want to become a stronger CEO, get in the room early and learn how it really works. It will transform the way you lead.

Here’s my full story.

The Challenge

The startup operated by selling video ads for $1,000. That was the complete offering. One-time service. Definitely not scalable.

The business was constrained by the typical service business model where time is traded for money, a product is created, delivered, and the focus moves to the next client. This approach has a ceiling that proves difficult to break through.

The Question

A simple question was posed to one of the customers:

“If I could get you actual users instead of just the video, what would you pay?”

Their response: “At least $5 per install.”

The follow-up: “Okay, if I got you 100K users, you’d pay $500K?”

Their answer: “Easily.”

That was when everything changed.

The Shift

The business model thinking shifted from video production shop to outcome delivery. The money wasn’t in the video. It was in what the video did: user acquisition.

The decision was made to go all-in on changing the business model to focus on outcomes. Instead of selling videos, the focus became selling results. Instead of charging for the creative work, the pricing structure changed to charge for the users delivered.

The Results

After a few years, that same customer was spending $10 million annually with the business.

This wasn’t “value capture.” It was simply asking a better question and aligning the offering with what the market needed. Same customer. Same industry. Completely different scale.

Conclusion

The transformation didn’t happen because core skills changed or new customers were found. The focus simply shifted from the thing that was made to the results it produced. This small change in perspective unlocked massive growth potential.

The fundamental principle: Don’t charge for the deliverable. Charge for the outcome. Customers don’t really want your product or service – they want the results it gives them. When pricing aligns with their desired outcomes, both parties achieve greater success.

These companies often follow the same pattern. A small team of three founders builds a minimum viable product in Cursor, avoids raising venture capital, and launches quickly. With no sales team and no marketing function, they go live, scale rapidly, and even reach profitability almost overnight.

This model is spreading fast. Everywhere you look, new startups are emerging with the same lean profile and eye-popping revenue. Some call it the future of entrepreneurship, while others use the term “seed-strapping.” But in truth, it is simply temporal arbitrage. These founders spotted a gap, shipped quickly, and took advantage of a market caught sleeping.

The Freeze

The problem is what happens next.

Instead of reinvesting their early traction into building real companies, many of these founders freeze:

• No hiring
• No scaling
• Just holding onto the false belief that the arbitrage will last

But it never does.

When Google can unveil 100 AI features at a single event, entire categories of these small startups are wiped out in an instant. Someone with 1,000 times the resources is always waiting in the wings.

The Real Question

The real question is how such startups can hope to compete if they never build defensibility or systems.

A real team provides advantages that three founders working in isolation cannot:

• Build depth
• Ship faster and with fewer bugs
• Invest in talent, infrastructure, and distribution
• Add customer support, sales, brand, and process
• Remove key-person risk (because duct tape can only hold things together for so long)

Fragile Foundations

Product-led growth is a strong starting point, but efficiency on its own is not a strategy. Remaining small may feel efficient, but it is not a sign of strength. On the contrary, it makes a startup fragile.

Even mergers and acquisitions become more difficult under this model. Without a real team to acquire, without meaningful intellectual property, and with only a thin feature supported by three people, there is very little of enduring value. Acquirers recognize that quickly.

Conclusion

$10M in ARR is an impressive beginning. But unless a true company is built around it, someone else will eventually take the opportunity. The lesson is clear: short-term arbitrage may deliver rapid traction, but only defensibility, systems, and teams create lasting value.

Here are the key takeaways from this article:

• Temporal arbitrage is not a sustainable strategy
• Efficiency alone cannot protect against competition
• Teams create depth, defensibility, and resilience
• Fragile startups are easily displaced when larger players move in
• Growth without investment in people and systems does not endure

If you want more insights on building beyond hype cycles and creating companies with staying power, follow me on LinkedIn by clicking here.

I had no product. No team. Just a slide deck and a few letters of intent from app developers who believed in a wild idea: short, in-app video trailers that would change how mobile apps acquire users.

That pitch turned into a $2M round from incredible investors like Charles Hudson, Jeff Clavier, Clint Chao, Maynard Webb, and Tim Draper.

That funding helped us launch Vungle, which went on to serve 100,000+ customers, generate hundreds of millions in revenue, and ultimately exit for $780M.

Today, for the first time, I’m sharing the original deck that made it all happen.

What Worked

We weren’t pitching a product. We were pitching a new category. Here’s what resonated:

• Anchoring on big shifts: mobile video, mobile ads, and the rapid growth of app developers
• Selling “why now” before “how”: timing mattered more than features
• Showing real ROI: one early partner saw a 9% CTR vs the industry average of 0.3%
• Revenue before product: we booked early revenue before we even built
• Plain English: we explained the business model and edge simply and clearly

The Original Deck

The slides walked through the problem, the new ad format we envisioned, early traction, and our plan to build a scalable process for video ads.

What stood out wasn’t the polish. It was the conviction that mobile apps needed a better way to reach users, and that video was the answer.

Lessons for Founders

If you’re a founder raising with nothing but belief and bold vision, remember:

• Big market shifts matter
• Show why the world needs your idea now
• Early validation, no matter how small, can make your story real
• Simple explanations beat complex ones

Conclusion

That first $2M didn’t come from having it all figured out. It came from selling a vision with just enough proof to make it believable.

The journey from a single deck to a $780M exit shows what can happen when timing, conviction, and early customer belief all align.

Here are my key takeaways from this experience:

• You do not need a finished product to raise funding
• Timing and market shifts are more important than features
• Early traction and revenue, even small, build credibility
• Simplicity in storytelling wins

Raising capital is never easy, but clarity of vision and strong conviction can open doors.

If you want to see more insights like this, including my Series A and B decks, follow me on LinkedIn by clicking here.

I guess this is what it means to be a Founder again.

30lb weight gain, back pain and pre-diabetes.

Before all this, I was a VC.

The VC Life

Gym 5 times a week, yoga and walks through nature.

Long vacations, especially Thanksgiving through New Year.

Portfolio catch-ups with Founders to show empathy and encourage them to keep trying.

The Reality Now

Now? I wake up from nightmares where Sam Altman just made an announcement that killed me plus 1000 AI startups.

I used to sound so composed with my British accent.

Now I sound like some poorly-educated hooligan.

I have lost count of the number of f-bombs I drop before lunch.

Running on Adrenaline

Yes, I am running on pure adrenaline.

I know this pace is not sustainable.

But this is what it means to feel so alive.

To be fueled with purpose.

Disrupting an industry demands your soul and every waking breath.

Conclusion

So here is to all the Founders out there, the crazy ones. This is what it really takes to build something that matters.

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Requiring employees to be in-person five times a week is critical when you are at the 0-1 stage.

You cannot match the speed and quality of execution when you have a team who can ideate with you and get things done.

Remote Work

Remote work requires infrastructure, process, and patience.

Why introduce so much friction?

My Experience

I have done two startups remote and both failed.

I have done two startups in-person.

The first was a huge success.

The second is my current company.

Future Plans

Once we are beyond the turbulent 0-1 stage, I would love to go hybrid or remote.

But right now, this company will not get off the ground unless we are in-person, five days a week, in a real office.

Conclusion

In my experience, early stage startups need the speed and execution that only in-person collaboration can provide. Remote work adds too much friction when you are trying to go from zero to one.

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I never did background checks on startup Founders until a bigger VC uncovered some dirt on my intro.

It was an expensive lesson in due diligence that changed how I evaluate people forever.

The Call

I had referred a Founder to a large VC fund which quickly turned into a signed term sheet.

I was super excited and was also going to invest.

The deal was deep in due diligence.

Thursday at 10pm, the main Partner calls me: "Zain, how well do you really know this guy?"

I had met this Founder many times.

He seemed like a nice guy.

Why is he getting cold feet?

"Well, this guy has sued so many people. Like 10 plus times. Find out what is going on."

My Mistake

I did not think that was a big deal.

I mean he is the plaintiff.

He probably got scammed right?

So next morning, I asked the Founder if there are any disputes or issues that he should disclose.

Well, at first, he played dumb and confused.

I let him know that all his lawsuits are a public record and I need straight up honesty.

And that is when things turned real nasty.

The Blowup

He went ballistic on me.

He even threatened to sue me and then hung up.

How ironic, right?

What I Learned

I learned a lot through that experience:

• Always do background checks on anyone you are doing business with or even hiring.
• Think twice before you officially sue someone in court. It might feel gratifying but it also creates a paper trail that can hurt you one day.
• Avoid overly litigious and vindictive people.
• Always disclose potential issues upfront.
• Do not make referrals to VCs unless you really know the Founder. It can make you look bad otherwise.
• Lawyers are the only winners in lawsuits.

The Twist

We are all conditioned to avoid people who have been sued as the defendant as that is a signal they must have REALLY done something bad.

I bet you did not think about the opposite side of this as a bad thing, did you?

Conclusion

Background checks are not optional in business, they are essential. A pattern of lawsuits, even as the plaintiff, can reveal more about someone's character than their pitch deck ever will. Protect your reputation by doing the homework before making introductions.

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I have seen a lot of advice lately telling first-time founders to bootstrap their companies.

I want to share a different perspective based on my own experience as a repeat founder with an exit.

My Honest Take

This is my opinion as a repeat founder with an exit behind me.

Most post-exit founders I know want to own 100 percent of their next startup.

They do not want the pressure from VCs.

They want to control their own destiny.

The Bootstrap Problem

Yet every LinkedIn post recently promotes bootstrapping as some universal law first-time founders should follow.

This is not good advice.

Founders with an exit already have some cash reserves.

They can always raise money easier on better terms so they take their time and wait.

The Reality Check

If you try to bootstrap your own company as a first-time founder, you are in for a world of pain.

You will likely run out of money and then you are in trouble for real.

Even if you do get profitable, you will end up competing with experienced founders who are also bootstrapping their company.

These founders will likely out-execute you and make fewer mistakes, especially with their deep domain experience.

Outspend Them

So the only way to beat them is to outspend them from the start.

VC funding is the way.

It allows you to make more mistakes, hire more people and increase your odds of winning.

If you get good VCs, you can also benefit from their experience (good VCs are often repeat founders).

Conclusion

If you are a first-time founder, go try and raise as much money as possible.

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