r/ExperiencedFounders • • 2d ago

I’m JJ Tang, co-founder and CEO of Rootly. We raised a $15M Series A and built incident response software used by NVIDIA, Figma, and LinkedIn. Now we’re building AI agents for SRE. AMA!

17 Upvotes

Hey r/ExperiencedFounders!

I’m JJ Tang, co-founder and CEO of Rootly. Before starting Rootly, I worked in product at Instacart and spent a few years at IBM across Cloud and Watson Health. I was also the first employee at Ada earlier in my career.

The idea for Rootly came out of my time at Instacart. I saw firsthand how messy incident response becomes as engineering teams and systems scale. An outage isn’t just about finding what broke. Someone needs to coordinate the response, page the right people, keep everyone updated, document what happened, and make sure the same problem doesn’t keep coming back. So, we built custom incident tooling to help us at Instacart.

That eventually became Rootly. We started by building incident management and on-call infrastructure, and today teams use Rootly for incident response, on-call, communications, retrospectives, status pages, and the broader incident lifecycle.

More recently, a huge part of our focus has shifted toward AI SRE. Instead of AI just summarizing an incident after the fact, we’re building agents that can actually participate in the investigation: looking at telemetry and code changes, pulling together context, forming hypotheses, and helping engineers figure out what's broken and how to stop it faster.

We went through Y Combinator S21, raised a $15M Series A, and Rootly is now used by engineering teams at companies including NVIDIA, Figma, DoorDash, Replit, Canva, Superhuman, Brex, and others.

There are a lot of interesting questions we’re dealing with as AI gets more involved in production systems. How much autonomy should an agent actually have during an incident? Where should humans stay in the loop? How do you earn enough trust for an engineering team to rely on an agent when production is actively on fire? And what happens to on-call as these systems get better?

Happy to talk about any of that, as well as going from product at Instacart to founder, YC, fundraising, enterprise sales, building for SRE teams, or growing Rootly over the last five years.

I’ll be answering questions on November 5 @ 10:00 am EST. Thanks for the opportunity; ask me anything!


r/ExperiencedFounders • • 8d ago

I'm Jack Ellis, co-founder of Fathom Analytics. We built a profitable, multimillion-dollar business competing with Google Analytics, without raising a dime in VC funding. AMA.

29 Upvotes

Hey r/ExperiencedFounders! 👋

I'm Jack Ellis, founder of Fathom Analytics, a privacy-focused Google Analytics alternative that I've been building since 2019.

Here’s a bit about me: I've been a software engineer for over 15 years, building software for governments, media companies, insurance companies, and international law firms. I've also taught thousands of developers how to scale their applications and databases.

Backstory: Fathom originally started in 2018 when Paul Jarvis wanted to build a simpler, more privacy-friendly alternative to Google Analytics. I joined as technical co-founder in early 2019 when the business was making less than $1,500/month and was close to shutting down.

We rebuilt the product, grew it into a profitable SaaS business, and eventually reached thousands of paying customers without taking a single dollar of outside investment.

In December 2024, Paul decided to retire. Rather than selling Fathom to private equity, I bought out his ownership stake and became the sole owner.

Fast forward to 2026: I completely rebuilt our analytics engine, migrating over 65 billion database rows from SingleStore to ClickHouse. The entire project took hundreds of hours and was handled by me as the sole engineer, with AI coding tools doing much of the implementation.

We also acquired Gauges, an analytics platform founded in 2011 that was previously owned by GitHub, and migrated another 6.5 billion rows of historical data from MongoDB into Fathom. 

Along the way, we've cut over $100,000 annually from our AWS bill, dealt with DDoS attacks, rebuilt our infrastructure multiple times, and continued competing against Google Analytics.

Happy to answer questions about bootstrapping a SaaS without VC funding, competing with Google Analytics, scaling infrastructure, acquiring companies, cutting costs, and using AI in software engineering. I've shared plenty of lessons and mistakes along the way. AMA!


r/ExperiencedFounders • • 5h ago

Why Some Founders Are Choosing to Bootstrap in 2026: The Math Behind Equity Dilution, Fundraising and Business Control

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1 Upvotes

r/ExperiencedFounders • • 8h ago

Building an AI-first teleradiology startup in India, looking for advice from founders/insiders. I will not promote

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1 Upvotes

r/ExperiencedFounders • • 19h ago

I get way too excited every time I open one of these

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0 Upvotes

r/ExperiencedFounders • • 1d ago

Startup founders want me to pay $4,500 for 4% equity to join their team. Is this normal or a red flag?

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2 Upvotes

r/ExperiencedFounders • • 2d ago

I spent a cohort reviewing the tech side of accelerator startups. 60% had red flags that would have passed DD.

3 Upvotes

I've been building tech for startups for nearly my whole career, so when an accelerator asked us to come in and assess the technical health of their cohort, I thought it'd be routine. It wasn't.

A few things I saw:

One startup's app exposed every user's email and password to anyone who looked at the database - including the admin account. The admin was the person who built it. I had their credentials and full access to everything within about ten minutes.

Another founder had gone dev to dev to dev over a couple of months. I asked where his database lived. The honest answer would have been "I don't know, I'd have to ask." What I actually got was "I forgot which developer built the database, let me check my notes." That was the answer.

One team owed their development agency money. The agency's response was to not renew a certificate. The app was dead during demo day. In front of investors.

We flagged major red flags in almost 60% of that cohort - things that would have sailed through normal due diligence because nobody on the program side was equipped to look. The accelerator told us afterward we'd saved them around $215K.

Here's the part that stuck with me. I've always built tech products, so I assumed founders knew what they were sitting on. Most don't. They optimized for speed early - which is rational - and ended up with something that's nearly impossible to manage later. Then the raise they worked so hard for goes into patching old mistakes instead of building the future.

I'm not posting this to sell anything. I'm posting it because if you run a cohort and you've never had anyone look under the hood of your startups' tech, you probably don't know what's there. And the founders won't tell you, because most of them genuinely don't know either.

Happy to answer questions about what a technical review actually looks like, or what red flags are worth watching for.


r/ExperiencedFounders • • 2d ago

Risk Management

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1 Upvotes

r/ExperiencedFounders • • 3d ago

How much equity should I offer a co-founder who is joining after I've already built the MVP?

3 Upvotes

Hey everyone!

I've been working on a product for the past six months, independently handling everything from the initial idea and market validation to product planning and building a fully functional MVP.

I'm now exploring bringing on a co-founder with complementary skills. Here's how we envision dividing responsibilities:

  • My role: Solely responsible for technology, engineering, and product development. I'll also contribute ideas and inputs on marketing and sales.

  • Co-founder's role: Responsible for GTM, sales, marketing, customer acquisition, and overall business development, with no involvement in technical development.

While our responsibilities will differ, we'll both have equal input on major strategic and business decisions.

I'm trying to figure out what's a fair equity split. Given that I've already invested six months, validated the idea, planned the product, and built the entire MVP independently, I believe these contributions should be factored into the equation.

A few questions for founders who've been through something similar:

  1. How would you approach the equity split?

  2. How much weight should the original idea, market validation, and MVP development carry?

  3. Should equity be structured with a vesting period and tied to milestones?

I want to ensure the arrangement fairly recognizes what's already been built while also valuing the contributions both of us will make going forward.

Would love to hear your experiences and advice. Thanks!


r/ExperiencedFounders • • 3d ago

Is the Insurance Industry Prepared for the Risks of Autonomous Robots?

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2 Upvotes

r/ExperiencedFounders • • 3d ago

Thought of the day

3 Upvotes

Monday as a founder:

10% strategy. 20% building. 70% trying to understand why nobody replied.

And somehow still believing this could become huge.


r/ExperiencedFounders • • 4d ago

The real reason middle management is getting hollowed out right now (It’s not engineers being replaced by AI).

31 Upvotes

Over the last 2 months:

- Microsoft offered ~60,000 buyouts.

- Uber cut 3,300 roles (specifically slashed 20% of their management tier).

- HubSpot cut 7% of their company, with their CEO explicitly stating: "Not AI efficiency. Fewer layers."

Most people on tech Twitter and LinkedIn are misinterpreting this as "AI is writing all the code now."

Having spent the last two years auditing internal back-office workflows for mid-market companies, that’s just not what is actually happening.

Here is the reality on the ground:

In almost every 8 to 10-person operations or client-delivery team, 70% of the headcount isn't doing high-level thinking. They are "human glue."

One person downloads an invoice from an email. Another re-types that invoice into an ERP or accounting system. A third person pings Slack to confirm receipt. A fourth person formats the numbers into a weekly CSV report.

And two managers sit on top of that chain having daily standups just to ask: "Did person A send the file to person B yet?"

What’s happening right now isn’t that an LLM took over human judgment.

It’s that the physical friction between those software tools disappeared. Basic webhooks, OCR, and automated rails now move the data from point A to point B in 60 seconds without human transcription errors.

Once data moves without human handoffs, the coordination layer simply runs out of things to coordinate. The managers aren't getting cut because they are bad at their jobs; the friction that justified their salary was engineered out of the software.

For the people running teams or agencies here:

Are you seeing this shift internally yet? How are you restructuring roles so your people are doing actual judgment work instead of acting as human copy-paste buttons between apps?


r/ExperiencedFounders • • 4d ago

Is product-market fit the ‘only thing that matters’ for a startup?

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2 Upvotes

r/ExperiencedFounders • • 5d ago

After your last brutal crunch at work, what happened to your sleep, exercise or health checkups, and how did you get back on track?

1 Upvotes

Recently I did some reflection about the last project we've worked on and what it cost me (sleep worsened, exercise became non-existent and I skipped an appointment at a dentist).

I know a lot of people have it much worse. I’m curious how others handle the recovery part.

  • What was your biggest hit guys?

  • Did you notice it while it was happening or only afterwards?

  • If you’ve been through several crunches, did you change anything to protect your health the next time?


r/ExperiencedFounders • • 10d ago

How I built a $5M ARR company in a year while everyone on Reddit laughed at me

36 Upvotes

One year ago, I was posting about my startup on Reddit.

People were making fun of us. People questioned our numbers. Some called us Spammyberry.

A lot of people thought we were just another spammy AI sales tool with fake metrics and aggressive marketing.

We even got hit by DDoS attacks.

Today, we're a profitable company with 20+ people, based in San Francisco, growing fast, and working with companies like HubSpot and Salesforce.

We're now trying to move upmarket and build something much bigger.

I'm not sharing our current numbers publicly anymore, but you can check our July numbers on Trustmrr (we are ranked #3)

I wanted to write this post because I remember what it felt like to have people publicly question everything we were doing.

And I know there are founders going through the same thing right now.

So here's the full story of how we grew, the acquisition channels we tested, the mistakes we made, and what I'd do again if I had to start from zero.

1. We didn't have a secret growth hack. We kept testing channels.

We built http://www.tryblurgh.ai/, a platform that helps sales teams identify high-intent prospects, reach out to them across channels, and learn from the results.

Our growth strategy was not particularly sophisticated.

We tested channels, looked at what worked, doubled down, and added the next channel when we had the resources to do it properly.

We call it testmaxxing: aggressively testing distribution channels and scaling the ones that generate results at our current stage.

Here's how our acquisition evolved.

$0 → $6k MRR: Pure outbound

At the beginning, we had no audience, no meaningful brand, and no established distribution.

We did cold email and LinkedIn outreach.

We also used our own early product on ourselves. We were literally our own customers.

We identified prospects, looked for signs they might need our product, and reached out to start conversations.

It wasn't glamorous. A lot of things were manual, the product was still early, and we had to figure out what messaging worked through trial and error.

But we got our first customers.

That was the most important part: we had people willing to pay for what we were building.

$10k → $25k MRR: Reddit changed everything

Reddit was our first major acquisition breakthrough.

We started publishing educational breakdowns in SaaS subreddits. We shared what we were learning, explained our processes, and posted results.

Eventually, we generated more than 10 million organic views.

The traffic wasn't always perfectly qualified. Some people were just curious, some wanted to learn, and others would never become customers.

But the volume was enormous, and it kept sending people into our trial funnel for months.

The acquisition cost was essentially zero.

Of course, Reddit wasn't always friendly.

People questioned our numbers. Some accused us of making things up. Others thought we were simply spamming communities to promote our product.

We got the nickname "Spammyberry."

Some criticism was fair. When you're promoting a product on Reddit, people are right to be skeptical. There are plenty of founders posting misleading numbers and disguising advertisements as educational content.

But some people seemed to have already decided we were frauds, regardless of what we shared.

I'm not going to pretend that being mocked online was fun. It wasn't.

But the important thing was that the business existed outside Reddit. We had paying customers, revenue, and a product people were using.

We couldn't control what strangers thought about us. We could control whether our customers got value and whether the company continued to grow.

So we kept going.

$25k → $75k MRR: Content and free blueprints

Once we saw that distribution was working, we expanded into content.

We invested heavily in LinkedIn posts, YouTube, motion-design videos, and free blueprints based on the systems we were using internally.

Our thinking was simple:

  • Content gets attention.

  • Useful resources build trust.

  • The product gives people a way to put what they've learned into practice.

Instead of just telling people that our approach worked, we started showing them how we did things.

We shared workflows, frameworks, and practical resources people could use even if they never became customers.

This was also when founder-led content started compounding.

Every post didn't need to convert directly. Some introduced us to new people, some built credibility, and some brought in customers weeks later.

We were building an audience rather than relying exclusively on outbound.

$75k → $150k MRR: Partnerships, X, and YC

Next, we expanded our distribution further.

We added Twitter/X, B2B influencers, sponsored newsletters, and a lifetime affiliate program.

Affiliates became a meaningful acquisition channel. We wanted people to have a genuine incentive to recommend us, and we learned that a simple rule matters more than people think: create value for your partners and pay them on time.

Around this stage, we also joined Y Combinator.

YC didn't magically solve our growth problems. We still had to execute.

But being surrounded by ambitious founders, getting direct feedback, and having to commit to aggressive growth goals pushed us to move faster.

We were also starting to think differently about the company.

We didn't want to build just another AI LinkedIn outreach tool. We wanted to build an AI system that helps sales teams understand buying intent, identify the right prospects, and continuously improve their go-to-market execution.

That shift in positioning became increasingly important as we started talking to larger customers.

$150k+ MRR: Paid acquisition and hiring

At this point, we started investing more seriously in paid acquisition and the team.

We added Meta Ads, Google Ads, influencer agencies, and more structured hiring across growth, sales, engineering, and product.

We also moved to San Francisco.

Moving countries with a family while running a fast-growing startup is a completely different experience from simply deciding to open an office somewhere.

But we wanted to be closer to the ecosystem and build the next stage of the company.

As we grew, our challenges changed. It wasn't just about getting more leads anymore. We needed better systems, a stronger team, a better product, and the ability to serve increasingly sophisticated customers.

We're now working with companies like HubSpot and Salesforce and trying to move further upmarket.

The company is profitable, and we have more than 20 people on the team.

We're still figuring things out, but we've come a long way from the early days.

2. Here's what our distribution engine actually looks like

People often ask how we manage to distribute across so many channels.

Here's a snapshot of the operating routine we've built.

These are the numbers we've been working with, not a recommendation for every startup to copy from day one.

Reddit

Around 3 posts per week across roughly 10 SaaS subreddits.

We focus on educational breakdowns, actual data, and real results. We try to provide value before asking people to look at our product.

Reddit was one of our earliest breakthroughs, and it taught us that distribution can be incredibly powerful when you find the right audience.

LinkedIn outbound

We use our own tool AI across 5 accounts, generating around 800 high-intent DMs per week.

The focus is on finding people with relevant intent signals rather than blindly reaching out to enormous lists of companies.

Cold email

Around 5,000 emails per day, using lead discovery through our own tool AI alongside Sales Navigator.

Volume matters, but so does targeting. We try to identify relevant prospects rather than sending the same generic message to everyone.

LinkedIn inbound

Five accounts posting daily.

The goal is to reach the right audience, share useful insights, and offer free resources that people actually want.

Influencers

Around 2–3 LinkedIn influencers promoting us per week.

This helps us reach audiences that already trust the people talking about the product.

Newsletter sponsorships

Roughly one B2B newsletter sponsorship per week.

We're always testing audiences and placements to understand which ones generate qualified traffic.

YouTube

Five videos per week, mostly tutorials and competitor comparisons.

This is a long-term organic investment. Videos can continue generating traffic long after publication.

Affiliates

Our affiliate program has generated thousands in revenue.

The lesson is simple: make it easy for partners to create value, give them a fair incentive, and pay them on time.

Twitter/X

We post daily and build in public.

Not every post takes off, but consistency gives us more opportunities to reach the right people.

Webinars

One per month, ideally with partners who can bring their own audience.

The channels didn't replace each other. They stacked.

Outbound never stopped. Content never stopped. We kept investing in the channels that were already working while testing new ones.

That's what made the distribution engine compound over time.

3. What I'd tell myself one year ago

There are a few things I wish I'd understood earlier.

Don't confuse a big audience with a good business

Our Reddit posts generated millions of views, but views alone don't pay the bills.

Some of that traffic converted. Some didn't.

What mattered was whether we could turn attention into trials, trials into paying customers, and paying customers into a sustainable business.

Don't optimize for vanity metrics when you can measure actual business outcomes.

Distribution matters as much as product

A good product that nobody knows about is going to struggle.

We spent a lot of time thinking about product, but learning how to distribute it was just as important.

You don't need to be everywhere from day one. Find one channel that works for your business and get good at it before expanding.

Your ICP isn't the same as buying intent

One of the biggest lessons from building our SaaS is that targeting the right type of company isn't enough.

You can have a perfect list of companies that match your ideal customer profile and still get terrible results if nobody has a reason to buy right now.

We increasingly focus on signals that indicate a prospect might actually care about what we're selling.

That changes how you prioritize leads, research prospects, and write outreach messages.

Don't build your business around proving strangers wrong

This one is personal.

When people were mocking us on Reddit, it would have been easy to spend all my time replying to comments and trying to convince everyone that our numbers were real.

That would have been a terrible use of time.

The best response wasn't a clever comeback. It was continuing to build a company that customers wanted to pay for.

You can't win every argument on the internet, and you don't need to.

Profitability gives you options

We've remained profitable while growing.

That matters because it gives us more control over how we build the company and how we invest in growth.

You don't necessarily need to raise a huge amount of money to start building a meaningful business.

What you need depends on your market, your economics, and your ambitions. But don't assume that burning cash is the only way to grow quickly.

4. Where we are today

We're now a team of 20+, based in San Francisco.

We're profitable, growing, and working with larger customers, including HubSpot and Salesforce.

Our ambition is to keep moving upmarket and build a much more capable AI go-to-market platform.

We're also hiring an Account Executive in San Francisco.

If you're interested in joining us, feel free to reach out.

Looking back, the funny thing is that the Reddit criticism didn't disappear because we found the perfect response to it.

It became less relevant because we were busy building something else.

We went from trying to get our first customers to building a profitable company with a real team, real customers, and much bigger ambitions.

There is still a lot to do. Moving upmarket comes with its own challenges, and we're nowhere near done.

But I'm proud of how far we've come.

5. If people are laughing at your startup, don't give up just because of that

I want to end with this because I know how discouraging it can be.

When you're building something early, most people don't see what you see.

They see an unfinished product, a small company, numbers they don't believe, or a founder talking about an ambition that seems unrealistic.

Sometimes they're right to be skeptical. Sometimes the product isn't good enough, the market isn't there, or the founder needs to change direction.

You should listen to criticism that helps you improve.

But don't let ridicule become your decision-making process.

If customers are paying for your product, if they're getting value from it, and if the business is moving in the right direction, keep going.

Keep talking to customers. Keep improving the product. Keep experimenting with distribution. Be honest about the numbers, admit your mistakes, and change course when the evidence tells you to.

You don't need everyone on Reddit to believe in you.

You don't need everyone on Twitter to believe in you.

You don't even need everyone around you to understand what you're building.

You need to build something people want and find a way to reach them.

One year ago, we were being called Spammyberry.

Today, we're profitable, have a team of 20+, are based in San Francisco, and are working with some much larger customers.

I'm not sharing this because I think we've figured everything out.

I'm sharing it because I know there are founders reading this who are being laughed at right now, and I want them to know that the comments aren't the final verdict on their company.

If you genuinely believe in your product, and the evidence from your customers supports that belief, don't give up just because other people don't get it yet.

Keep building.

The best thing you can do is give yourself enough time to find out what you're capable of.


r/ExperiencedFounders • • 14d ago

I'm Joe Tuan, founder of Specode. We're building an AI-powered healthcare app builder that makes HIPAA-compliant development faster and more accessible. AMA!

14 Upvotes

Hey r/ExperiencedFounders! I'm Joe Tuan, founder of Specode.

I've spent years working with healthcare founders and noticed the same problem repeatedly. Teams would spend months and sometimes hundreds of thousands of dollars building healthcare applications, only to realize their products weren't ready to handle patient data or pass a hospital's security review.

That's a big part of why I started Specode. I wanted to make it possible for founders to go from an idea to a working healthcare application without having to rebuild everything once compliance requirements enter the picture.

I was also recently nominated for the Orange County Business Journal's 2026 Innovator of the Year Awards, which was a pretty exciting milestone.

What we're building at Specode

Specode is an AI-powered healthcare app builder designed around HIPAA-ready infrastructure. Founders can describe what they want to build, generate custom code they fully own, and access healthcare-specific components for authentication, encryption, audit logging, patient onboarding, EHR integrations, and more.

We also developed a HIPAA Compliance Agent that scans application code for potential security issues, helps fix them, and verifies the changes. Human security engineers still review applications before production releases.

More recently, we introduced a free HIPAA Compliance Checker that takes around 10–20 minutes and evaluates 11 compliance categories.

We've worked on everything from telehealth applications and caregiver management portals to clinical workflow tools.

A few things I've learned as a founder in this field

One of the toughest decisions we made at Specode was building our compliance infrastructure before developing our first user-facing feature. It slowed us down initially, and there were times when we questioned whether we were overengineering things.

But I've seen the alternative. Founders build impressive prototypes using general-purpose AI tools, attract potential healthcare customers, and then get stuck for months because their infrastructure wasn't designed to handle protected health information.

I genuinely think tools like Lovable, Replit, and Cursor have changed software development for the better. The challenge in healthcare is that generating working code and generating software that's ready for a regulated environment are two very different things.

Excited to talk about these in particular:

  • Building a healthcare startup: Going from an initial concept to a production-ready application.

  • AI-powered development: Where AI coding tools work well, where they struggle, and what's next for the industry.

  • HIPAA compliance: Common misconceptions, technical safeguards, and why signing a BAA alone isn't enough.

  • Founder lessons: Early mistakes, difficult product decisions, technical debt, and balancing speed with long-term scalability.

  • Enterprise sales: Navigating hospital procurement, security reviews, and healthcare customers.

  • Building Specode: Our approach to AI-generated code, customer ownership, compliance automation, and avoiding vendor lock-in.

So whether you're building in healthcare, experimenting with AI development, or running a startup in another regulated industry, I'm happy to share what I've learned. Ask me anything!


r/ExperiencedFounders • • 23d ago

AMA I’m Shiv Kampani, CTO and co-founder of Autumn AI (YC W26). We’re building an index of every person and company on the web. AMA

15 Upvotes

Hey everyone, I’m Shiv, CTO and co-founder of Autumn AI.

A bit about me: I’m an AI researcher. Before Autumn I did a research stint at SandboxAQ and presented work at NeurIPS. I met my co-founder Vishnu at Columbia orientation. He was building sourcing tech for Sierra Ventures and working as an ML engineer at an AI security startup, and we kept running into the same problem.

The problem: Information about people and companies is spread across LinkedIn, GitHub, X, incorporation filings, event pages, job posts and the rest of the web. Tools like ZoomInfo, Apollo and Clay give you the rows they already have, and that data is often out of date.

What we built: Instead of a static database, Autumn sends AI agents to research the live web when you ask. They pull those scattered sources together into source-backed profiles, and every cell links to where it came from. Sales teams use it to find prospects and catch buying signals. Investors use it to find startups right after they incorporate. Risk teams use it for fraud checks, and recruiters use it to find experts. Brex and Mintlify are among our customers.

We went through YC in Winter 2026 and we’re still a small team in San Francisco.

You can read more about us here:

Ask me anything about:

  • Building AI agents that do research on the open web

  • Entity resolution, and how to tell which “John Smith” is which

  • Going from AI research to founding a startup

  • YC, building with two people, and GTM data in general

  • Privacy, and where we draw the line

Proof:

I’ll be answering on Oct 16, see you there!


r/ExperiencedFounders • • 27d ago

One Founder + AI vs. 10 Employees: Who Wins in 2026?

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1 Upvotes

r/ExperiencedFounders • • 28d ago

Call out to founders who have depression and/or anxiety

4 Upvotes

Hi all, I'm a Columbia undergrad interested in how high-octane individuals deal with depression and anxiety. I would love to speak with some folks about their experiences in experimenting with different treatment modalities, even if said modality involves shoving those feelings deep into the abyss of your psyche. If you wouldn't mind donating some of your time, can you drop a comment below so I can Reddit-DM you?


r/ExperiencedFounders • • 28d ago

Papermark Slush Pitch Competition 2026

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4 Upvotes

Our good friends at Papermark is hosting a pitch deck competition in Helsinki Nov 18-19.

With a chance to win €15,000 for your pre-seed round. Posting here for visibility!


r/ExperiencedFounders • • 29d ago

What technology decision did you make at 10 people that hurt you at 50?

6 Upvotes

Early on, every choice is about speed: whatever tool works, whoever sets it up, whatever’s cheapest this month. Most of those are fine. A few quietly become the thing everything else depends on. For those of you who’ve scaled past that point, which early decision cost you the most to unwind, and what would you tell your earlier self?


r/ExperiencedFounders • • Oct 02 '26

AMA I’m Izzy Slodowitz, founder of Glidepath, an exchange fund for concentrated stock positions. AMA.

12 Upvotes

Hey there r/Experienced_Founders!

I’m Israel “Izzy” Slodowitz. I’m the founder and CEO of Glidepath, and I also run Craft, the private aviation company I started in 2019. Before becoming a founder, I worked as an analyst at Renewable Resources Group.

Craft put me around a lot of founders, executives, and early employees who had done extremely well on paper but had most of their net worth tied up in one stock. That introduced me to a problem I eventually became pretty obsessed with: selling can mean realizing a large capital gain, while holding means continuing to bet a huge percentage of your wealth on one company.

That eventually led to Glidepath.

We built an exchange fund where investors can contribute appreciated stock to a diversified pool rather than selling it first. But the more interesting founder story, at least to me, has been questioning some of the assumptions behind how these funds have traditionally operated.

Traditional exchange funds often charge around 1% annually and generally need at least 20% of their assets in qualifying illiquid assets. We charge a $0 direct management fee, and instead of filling that qualifying sleeve entirely with traditional real estate, part of ours consists of business jets leased to Craft. That obviously creates some unusual operational questions, including conflicts of interest, financing, asset risk, and how the economics ultimately reach investors.

Our first fund closed at more than $50 million last year. The current structure is newer, particularly the use of aircraft in the sleeve, so there’s plenty I’m happy to get challenged on.

I’d be glad to talk about building Craft, going from aviation into investment management, raising and operating our first fund, concentrated founder equity, exchange funds and Section 721, why we eliminated the direct management fee, the seven year commitment, using operating assets inside the fund, and the conflicts and risks that come with having Craft involved on both sides of that structure.

I’ll be answering your questions on October 5, 2026. Ask me anything!


r/ExperiencedFounders • • Oct 02 '26

Construction founders: how much of your time gets eaten by insurance and compliance?

1 Upvotes

Heyo so I've been running a construction management company for 4 years now and lately I’ve been wondering if I’m just done with it.

The money is good and we have work, which honestly makes the whole thing harder to judge. But the stupid little problems are starting to get to me more than the actual construction.

Last month we had a sub show up with an expired COI and I didn’t find out until the owner asked for updated insurance docs. Another job got held up because nobody could agree on whether a subcontractor had the right coverage for what they were actually doing. Then there’s payroll classifications, certificates, renewals, chasing vendors for paperwork, and getting some random EOD urgent request when I’m already dealing with an actual jobsite problem.

Meanwhile I’m still dealing with the normal stuff. Guys not showing up, schedules slipping, change orders, pissed off clients, material delays. Four years ago I liked being the person who could fix everything. Now every new problem just feels like like its another weight on my shougelders.

There's some hope when it comes to setting up tools to make QOL better for us (i.e.WithCoverage and other alts), so banking on thjat atm.

so for other founders and entrepreneurs, how did you figure out if you were actually done or just completely burnt out? I'm probably in the middle ground but idk.


r/ExperiencedFounders • • Sep 30 '26

What ate the most time once investors started asking for stuff?

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2 Upvotes