I just submitted my third application to Iterative. For my startup, Synscribe. It was a surreal feeling.

A part of my brain, the ego, immediately asked, “Really? We’re doing this again?”

Then I realized something.

The person who sent the first two applications isn’t me. The company he applied with isn’t this one. The fundamentals are different. The metrics are different. The resolve is different.

So this isn’t the third application. It’s the first time they’re seeing this version of me, and this company.

Then another question came up. Synscribe is operating off revenue. We’re in a good place. Do I really need to split my time and energy to apply to an accelerator? We can hire people. We can pay for courses that cost thousands. We can afford things.

A framework I learned from YC helped me think it through (also on Iterative's website). It boils the decision down to a single question: “Does this increase my average outcome by 11%?”

I think the answer is yes.

As a solo founder, I have blindspots. There are aspects of the business and opportunities I’m not even aware of. The community alone, for customers or employees, could be a huge help.

The best part about making the decision this way is that the outcome can only be positive.

One of two things will happen.

1. I get in. I get funds to accelerate growth, new friends, new perspectives, and a new network.

2. I get rejected a third time. I still get a new perspective on my business, and I can keep growing at the pace my revenue allows. I can always choose to try again later.

Either way, I learn something. Either way, I move forward.

I’m writing this down for two reasons. First, so I can come back in a year and see what’s changed. Second, to maybe inspire someone else to just take the shot.

Below is my application in full. I've redacted some financial information but otherwise everything is verbatim from the application. Also, I didn't use AI for the application to keep it real and raw (I found the last 2 to be 'too polished').

Date Submitted: 21 Nov

Company Description

Briefly describe your company. Should be 50 words or fewer.

Synscribe is an SEO company. We help growth stage startup win more customers organically from ChatGPT and Google. We specialise in programmatic SEO approach that help our customer score high intent customers. Customers can see results in as little as 5 days. At its core, Synscribe has an orchestrator that let human specialist work in parallel with AI agents. Over 90% of work is automated. 

Additional Materials / Pitch Deck

View on Google Slide

Additional Demos

This youtube short and this other plugin we use everyday

What need or opportunity are you addressing?

Describe the problem your company solves in 200 words or fewer.

Startup founders found it hard to crack their 2nd or 3rd growth lever (after usually after outbound sales & performance marketing / ugc)

Know that organic is the way to go but...
1. Conflicting information on the space (ie SEO vs GEO) -> decision paralysis
2. Market is full of low quality players -> low trust
3. High quality consultants do not have capacity -> high cost
4. Hiring in-house -> high uncertainty, slow ramp

How have you validated this need?

Include any concrete user studies or experiments that give you confidence that this problem is real and large.

Talking to growth stage startup showed us how messy revenue attribution are. Founders are running multiple growth strategies but have trouble attributing revenue to individual ones and do not know what to double down on. Often they know intuitively that SEO (or GEO) is the way to go but not sure how their agency work even bring them revenue. Customers are already in pain, paying for agency that games vanity metrics but cannot pull the plug on them due to fear of missing out. We win 9 of 10 deals when customer is ready-to-buy (ie done initial research & budget ready) and often at 50+% price premium.

How big is this problem?

Describe how your company becomes a $100M revenue business.

SEO tool has traditionally been a huge industry. Ahref is 100M+ ARR and Semrush was recently acquired for ~2B. These are just 'tools-only' businesses while the larger SEO service and organic marketing size of pie is much larger.

We start with an agency model with high touch with the customer to learn about how to execute flawlessly and produce results. This is the path of companies like Vanta. 

Unlike Vanta which which uses the cookie cutter model for 'form filling', creative and strategy work is a harder problem with greater reward. With more intelligent AI we are seeing new capabilities being unlocked by AI and we are creating a new model of autonomous AI agency starting with a hybrid model where AI and human work alongside each other. 

Instead of building the best SEO tool. We seek to devour the entire organic marketing consulting industry. 

What’s your unique insight, approach or advantage?

Describe what you know about the problem, solution or target audience that very few other people know or believe.

One, fear works better than greed. Founders fear:
- not being able to see how their growth levers impact revenue
- competitors eating away at their market share
- losing customers that should have been theirs

We give them certainty in the strategy and help them build internal tools to attribute revenue

Two, we now know more about SEO/GEO than most companies and have results to show:
- you don't need 3 months for SEO, we have so many 3 days old page ranking #1
- focus on the commercial intent keyword, there is likely 100 of ways your product can be described
- high quality content wins, your content stand out from the sea of AI slop. google can tell in the very first scan. 
- make friends, write about others, write to others, build content partnership, or just pay them off.
- own multiple assets to negotiate for better content partnership deals.
- there's no one-size-fit-all strategy when comes down to SEO, but we come very close to that and know when there should be variations.

Three, finding the right customer is 90% of the work. 10% of the work is applying our framework consistently and running new experiments to unlock higher value.

What do your users do now without your product?

Describe how what they do now is better or worse than what you’re doing - it could be another startup, spreadsheets, or even manual processes.

1. Doing SEO themselves (not our ICP, won't spend, moving too slow)
2. Paying for AI tools or hiring someone to do it - usually ended up having disgruntled and frustrated employees who doesn't see how their work move the needle. When metrics doesn't move or revenue cannot be attributed, there's no budget expansion but more work and more frustration. Some become clients when they see a better alternative. 
3. Hiring low-quality SEO agencies - usually get told to wait 3 months with no intermediate results and no additional insights to founder. Content produced are usually upper funnel and do not drive conversion. After a while there is uptick in clicks and impressions but they cannot be attributed to revenue. Founder is frustrated that SEO is inconclusive but fear missing out on growth opportunities if they pull the plug. We acquire Wonderchat this way when we get them to commit to running both agencies for 1 month in parallel and we will build their attribution. 
4. Hiring high-quality SEO consultants - these are usually recommended by word of mouth in close knit business owner or founder community. The price point are high (8-10k+) but they work. Most of these are available as consultants and helps build out the content team internally and will drop after a month or two and some of them do not help in the execution. These consultants usually do not have too much capacity to take on too many clients either. We usually come in when contract ends and founder is convinced that SEO works but need to scale on execution. One of our customer, Hyperbound, a YC company, came to us this way. 

How far along are you?

This typically includes core metrics like the number of users, monthly growth rate, revenue, etc.

Core Metrics
- Total: [redacted] MRR
- 7 customers for [redacted]k average monthly retainer
- Growth rate 30-50% MoM (last 3 month)

Technical Metrics:
- fully-autonomous content research and production that can create 100s of blogs per client per month
- fully-autonomous landing page creation that can create 100s of landing page per client per month
- fully-autonomous content partnership outreach that contact other sites when their content are being cited or when we load competitors backlinks in
- fully-autonomous company research tool that let us be 10x more prepared for every sales call and provide material to kickstart new customer account
- huge database (4k+) of site owner contacts and rates for off-site content placements that's growing each day

Others:
- recently onboarded first contract for e-commerce and unlocked new capabilities for pSEO on shopify store
- our network of client site we manage allow us to link sites from each other and negotiate for content partnership that otherwise would not be possible (even with money) 
- recently experimenting with using press release to supercharge SEO efforts. results were amazing, we got a brand new site propelled to the front page of google. 

Strategic:
- we have most of the components to launch a full self-service saas to unlock a large customer segment and is starting to ramp our marketing to build a wait list right now

How long have you been working on this and what have you learned about this need?

Tell us when you started working on this idea, and Describe what you have learned about the problem, the people who have that problem and your solution since starting to work on your startup. The more non-intuitive the better.

11 months where we only started seeing huge traction in the last 3 months. 

Initially I wanted to help anyone who wants help in getting organic traffic but realised that customer selection is really important. For the same amount of work, we can get a high growth startup 6-7 digit deals with less pain in the process as opposed to smaller companies that does not have a big market to grow into. For those group of non-ICPs, we intend to come back to them when we have other product offerings, so right now we keep them warm with our content.

Founders that are in the growth stage doesn't necessarily mean they have sorted it out. We've met so many founders who know nothing about attributing revenue and the ability to help them see was far more impactful than showing case studies after case studies. Eliminating uncertainty turns out to be super valuable.

If customers are not already spending, they are not going to be our customers. If they are spending time on researching the topic, speaking to right people, evaluating SEO agencies or tools or tried out SEO agencies, these are great signal. It's easier to get money to flow our direction than force money out of a rock.

Caveat to the insights above: if they spend too much time on the fence with analysis paralysis, they don't make good customers either.

Other insights:
- Forget marketing or building in the early stage, just sell -> provide value -> build -> find pattern
- I'm now more convinced than ever that the AI agency model is going to trump tools saas. margins are higher, customers are more satisfied and feedback loop is TIGHT.
- Drop the contract. Let customer drop if they don't see value. Now work on how to help them see value.
- Log down everything - How you work, how you think, when do you make what decision, where are the fine lines. These becomes the ultimate AI training material or company SOP. 
- Work with someone radically different in skills and interest but aligned in value. We'll hate different things and love different things and not stumble on each other.
- Hiring is a pain. I'm now optimizing for a can-do, positive attitude and high learning rate. The easiest way to tell is to hear them talk about the most interesting things they learnt or did in the last 2 months. And/or ask for a book recommendation. 
- Cash-flow wins. We can test out potential hires instead of sitting on candidates. We can gift our customers free press releases to test new approach that cost thousands (they loved it). We can pay for bleeding edge courses on AI evals that cost thousands. We can say no to people that do not align to our direction or value. 
- Ask "How hard can this be?". And then find out. And then hire people who do the same.
- Imposter syndrome is real. And it might never go away.

Update #1 - First Call Setup

Date of Notice: 25hth Nov (4 days after application)

A quick update to the above application. I've received an email from the admission team on the next step - a 20 min call to learn more about the company.

Have booked the first call on the 3rd Dec.

Update #2 - First Call with Investment Team

Date of Call: 3rd Dec (8 days from previous email)

I just got off the call with Cathy Guo, Head of Investments at Iterative.

If you’re expecting a casual chat where you walk them through your pitch deck slide-by-slide, this isn’t it.

The call was rapid-fire. It was clear she had already read through everything - the application, the deck, the memos.

We didn’t open the slides once.

The vibe was intense but real. At one point, Cathy mentioned a section of my application where I did a brain dump on my learnings—the good, the bad, and the ugly. She said it was a fun read. I told her, "That's how you know there's no AI in there."

Here is a breakdown of what they actually ask, and my takeaways from the process so far:

The Interrogation (The Good Kind)

The questions came fast. They aren't interested in the fluff; they want to know if you understand your own business mechanics. Here are the main buckets of questions she drilled into:

1. The "Why Now?" on Growth
She noticed the compound growth rate was decent (14%) since Jan, but exploded (50%+) in the last three months. She wanted to know exactly what changed.

• Who is the actual ICP? (Turns out it's not the fresh YC grads I thought it would be, but the 2-founder, efficient B2B startups in Singapore/NYC who hate hiring).

• Why do they stay? (We dug into retention. Apart from one early small client, nobody has dropped).

2. The Unit Economics
She drilled down into the contract sizes.

• You started at $x, now you’re at $y. How?

• How do you attribute revenue for them? (I had to walk through specific customer journeys).

3. The "Is It Real?" Test
We did a product walkthrough. This wasn't a polished demo; it was me showing the backend. I showed her the autonomous link-building tool and how the system "wakes me up" with partnership deals. I think this is crucial. At the stage where I'm at, they need to see that you’ve actually built the thing, not just mocked it up.

4. The Billion Dollar Question (The Hard Part)
This is where it gets tough. She asked:

• "What are the win conditions? What does the world look like if this becomes a $1B company?"

• "How do you get from $x to $y MRR in the next 18 months?"

Honestly, these are hard to answer when your hair is on fire. I think in terms of Bayesian probability—I have multiple bets (A larger, more efficient team, Self-serve, Shopify SEO, etc.), and I’ll figure out which one works. But when I'm the bottleneck, it’s hard to verbalize a 18 month vision when I'm just trying to hire your first ops guy so you can sleep.

I’m a big believer in the Theory of Constraints.

Right now, I am the constraint. If I solve that, growth happens and I've a new problem on my plate which is probably the sales pipeline. As long as I continue to identify the next biggest bottleneck and solving for it, growth is inevitable. The issue arise when you ask "Will you end up on a local minima?" (an optimization problem).

My bet is simply that the local minima is a great place to be in. And we will know how to nudge ourselves out of that at that point.

My Observations

1. Preparation is Key
They do their homework. If you get on a call with Iterative, assume they know your numbers better than you do. Don't waste time on the basics.

2. The "Crowded Market" Dilemma
Cathy brought up that this space is noisy. There are a million social media automation and content tools and plenty land on their desk looking for investments.

This is the Catch-22 of startups.

If there’s no competition, there might be no market. If there’s a lot of competition, it’s a bloodbath.

In a space this crowded, the investment thesis isn't "Is the market big?" or "Does the solution work?" (The market is clearly there).

The question is: "Is Raymond the person who will out-maneuver everyone else?"

3. Being Real Helps

I didn’t try to pretend I had a master plan for every single variable. When she asked about the team, I was honest about the struggle to find people who meet my standards vs. the need to just get bodies in seats. I think that honesty landed better than a rehearsed "we are scaling rapidly" speech.

Now, we wait. If I get a second call, it means they think I might be the one to win the market.

If not, I’ll keep building. Mainly allocating my energy to figure a way to remove the 'busy work' and move myself to more high leverage work by hiring.

OH YES I'M HIRING! If you are still here and know someone with the hustle, learn fast and is not afraid to roll up the sleeves and get down and dirty, send them my way.

Update #3 - Final Call Setup

Date of Email: 5th Dec (2 days from previous call)

A quick update. In just 2 days from the call with Cathy, I've received an email from the Brian Ma, GP at Iterative,on the next step - a 30 min call to learn more about the company.

Alongside the meeting invite they've prepared a short guide to prepare for the call.

As the guide is not publicly availble, I'll simply share the gist of the guide instead of the entire link (until I've recevied permission to share that publicly):

• the investment team have put together a comprehensive report opportunities, risks and challenges of this company

• there are 3 questions they want you to think through before the call

• they want to know what you want to achieve in the 3-4 months of the program so they can help you in the program

Update #4 - Final Interview Call with Brian Ma

Date of Call: 16th Dec (11 days from call setup email)

I just got off the final call with Brian Ma, GP at Iterative.

While the previous call with Cathy felt like a rapid-fire stress test of my metrics and past performance, this one felt completely different.

It wasn’t an interrogation.

It was a deep dive into the future and the first principles of the industry.

Here is the format of the call for me, the questions that came up, and how it compared to the preparation materials:

The Format: A "Jam Session" on Market Mechanics

The email invite came with a prep guide asking me to think about my "Win Conditions," "Growth Blockers," and "Program Goals." I spent roughly 45 mins putting together my raw thoughts on them.

And as expected, we didn't go through that list. We didn't open a pitch deck either.

Instead, Brian started with a candid admission: he knows SEO inside out, but "GEO" (Generative Engine Optimization) is new territory for him. The first 10 minutes wasn't a pitch; it was me explaining the fundamental shift in how search engines work today versus five years ago.

The Questions (What was actually asked)

The conversation wasn't about "What is your CAC?" or "What is your churn?" It was focused entirely on the validity of the thesis.

1. The "Teach Me" Question:

"I feel like I know exactly what to do to optimize for SEO. I have no clue what to do to optimize for GEO. What am I doing differently?"

He wanted to know if the solution was actually novel or just a buzzword. I had to explain the shift from optimizing for keywords ("VC Singapore") to optimizing for natural language & long-tailed queries ("Best B2B VC in Singapore for under $500k checks").

2. The "Is it Real?" Check

"Is there a product right now, or is it just services? Can I see it?"

I decided to skip the marketing fluff. I shared my screen and showed him the messy backend—the internal tools, the "landing page pillars," and the logs where our AI agents generate images and product mockups on the fly.

Hot tip: Looking back, it might have been more productive if I thought through the demo flow first. That way I would be able to focus on how some of the things we do in the product help us be the 1B company.

3. The Billion Dollar "Agency Trap"

"No SEO agency has ever become a billion-dollar company. They cap out at $100M. Tools like Ahrefs become billion-dollar companies. How does this become a billion-dollar company without hiring an army of consultants?"

This was the core friction of the interview. We spent some the time on the physics of the business model and what the model will look like in a post-AI era. My hypothesis was that AI changes the unit economics of a service business—moving it from a headcount-heavy model to a compute-heavy model and it has the ability to deliver and capture more value.

The "I Don't Know" Moment

Brian pushed hard on the scaling mechanics. He asked how we get from our current efficiency to the 100x efficiency required for a massive exit.

I didn't have a rehearsed answer for the endgame. I told him: "That is where my knowledge runs out."

I explained that I can clearly see the path to 20x efficiency, but I don't know what the machine looks like at 100x yet—and that I want to find out. Interestingly, this admission didn't kill the momentum.

The Investor's Mental Model

At the end, I asked him how he evaluates a company like this. He gave me a fascinating insight into his decision-making process.

He isn't asking "Is this risky?" (because all startups are risky).

He is asking: "Why now?"

In his words, we are seeing AI replace legal docs and finance workflows right now. His internal debate is whether this specific moment is when AI finally replaces the SEO consultant. If the answer is yes, the "Agency Ceiling" might finally be broken. If the answer is no, then it’s just a profitable cash-flow business, not a venture-scale one.

Status: The call ended with a "Give us a week."

Now, we wait...

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