đź’° Fundraising in the AI Bubble: $192B Invested, But Is It 1999 All Over Again?

Just spent the last 3 days at SF Tech Week hitting every VC event I could find. The fundraising landscape in late 2025 is… complicated. Let me share what I learned from the trenches. :roller_coaster:

Events attended:

  • Andreessen Horowitz “State of AI Funding” breakfast
  • YC Alumni “Surviving the AI Winter” panel
  • Sequoia “What We’re Funding Now” fireside chat
  • SPEEDRUN Demo Day (100+ AI startups pitching)

The Tale of Two Markets

The headline numbers look INSANE:

From Bloomberg report (Oct 2025):

  • $192.7B invested in AI startups in 2025 YTD
  • 70% of ALL VC dollars going to AI companies
  • Q3 2025: Global VC funding up 38% YoY
  • 498 AI unicorns valued at $2.7T combined

My reaction: “Great! Easy to raise, right?”

Reality check from a16z partner: “That money is going to 20 companies. Everyone else is fighting for scraps.”

The Concentration Problem

Data shared at Sequoia session:

Top 20 AI companies raised: $132B (69% of total)
Remaining 10,000+ AI startups raised: $60B (31% of total)

Mega-rounds dominate:

  • 69% of AI funding goes to rounds $100M+
  • These are growth-stage companies (Series C+)
  • OpenAI alone raised $30B+ in 2025

For seed/Series A founders like me:

  • Seed: $9B across 3,500 companies = $2.6M average
  • Series A (AI): $16M median (vs $7M for non-AI)
  • Series B+: Getting much harder unless you have monster traction

Translation: If you’re not OpenAI, Anthropic, or Perplexity, you’re competing with 10,000 other AI startups for 1/3 of the money.

What I Learned at SPEEDRUN Demo Day

100 AI startups pitched. Here’s what I observed:

Category breakdown:

  • AI agents/automation: 35%
  • Developer tools: 25%
  • Enterprise AI: 20%
  • Healthcare AI: 10%
  • Everything else: 10%

The pattern: 80% of pitches sounded IDENTICAL.

Typical pitch:
“We use AI to [common task]. We’re different because we have [minor technical detail]. We have $50K MRR and growing 15% month over month.”

VC feedback (overheard at after-party):
“I saw 30 companies doing essentially the same thing. Why would I bet on any of them when I can wait and see who wins?”

The brutal truth: Differentiation is REALLY hard when everyone has access to the same foundational models.

The “AI Winter” Warnings

The term “AI winter” came up in EVERY panel I attended.

Apollo Global Management economist (quoted everywhere):
“The current AI bubble is stronger than the dot-com boom. We’re looking at order-of-magnitude overvaluation.”

Sam Altman himself said (widely reported):
“The AI market is in a bubble. Investors are overexcited.”

Data that scared me from Yale professor’s analysis:

OpenAI case study:

  • Valuation: $340B (latest round)
  • 2025 revenue: $11B
  • Profitable by: 2029 (projected)
  • Cumulative losses 2023-2028: $44B

That’s a 31x revenue multiple for an unprofitable company.

Comparison:

  • Google at IPO: 10x revenue (profitable)
  • Amazon at peak bubble: 15x revenue
  • OpenAI today: 31x revenue (losing money)

Bain & Co. prediction (presented at a16z):

  • By 2030, AI companies need $2T annual revenue
  • Projected actual revenue: $1.2T
  • Gap: $800B shortfall

Question that keeps me up at night: When does this unwind?

The Funding Bar Has RISEN Dramatically

From YC Alumni panel:

YC acceptance rate: 1% (10,000 applications, 100 accepted per batch)

What used to work (2023):

  • Idea + founding team
  • Maybe a prototype
  • Raise $1-2M seed

What you need now (2025):

  • Live product
  • Paying customers
  • $50K+ MRR
  • Clear differentiation
  • Path to $100M ARR
  • Raise $2-4M seed

YC partner quote:
“In 2023, we funded ideas. In 2025, we fund traction. The bar has moved.”

Series A is even crazier:

2023: $5-10M ARR gets you a Series A
2025: $10-20M ARR gets you MAYBE a Series A

Sequoia partner:
“We’re seeing companies with $15M ARR struggling to raise Series A because investors are worried about market saturation.”

The Valuation Trap

Cautionary tale from a founder at after-party:

2024: Raised seed at $30M valuation (AI hype peak)
2025: Trying to raise Series A
Problem: Need to price at $100M+ to avoid down round
Reality: Investors offering $60M (based on actual metrics)
Result: Can’t raise, burning cash, might die

The trap:

  1. Raise at inflated valuation during hype
  2. Spend 18 months building
  3. Market corrects
  4. Can’t raise at reasonable valuation (down round scares investors)
  5. Run out of money

Advice from multiple VCs:
“Raise at reasonable valuations. Survive to the next round.”

What VCs Are Actually Funding

From 3 days of conversations, here’s what’s working:

1. Applied AI in boring industries

  • Healthcare workflows
  • Legal document processing
  • Manufacturing optimization
  • Logistics

Quote from investor:
“Everyone wants to build the next ChatGPT. We want companies applying ChatGPT to problems that make money.”

2. AI infrastructure/tools

  • Model evaluation platforms
  • AI observability
  • Cost optimization
  • Security for AI systems

Why: These have immediate, measurable ROI

3. Vertical AI agents

  • Sales automation
  • Customer support
  • Recruiting
  • Specific industry workflows

Must have: Clear ROI story, not just “it’s cool”

4. Companies with DEFENSE

  • Proprietary data
  • Unique distribution
  • Network effects
  • Switching costs

Not: “We fine-tuned GPT-4” (that’s not defensible)

Revenue Expectations Are Insane

Data shared at multiple events:

To raise in 2025, you need:

Seed ($2-4M):

  • $30-50K MRR
  • 10-20% month over month growth
  • 3-6 month runway from previous funding

Series A ($10-20M):

  • $1-2M ARR
  • Net retention 120%+
  • Path to $10M ARR in 18 months
  • Unit economics that work

Series B ($30-50M):

  • $10M ARR
  • Growing 3x year over year
  • Clear path to $100M ARR
  • Proven go-to-market

These numbers were unthinkable 2 years ago.

YC data point:
“25% of our current batch has 95% of code written by AI. These founders don’t need 50 engineers.”

Implication: You can get to revenue faster with less capital, so investors EXPECT more traction earlier.

The Profitability Pressure

MAJOR shift I’m seeing:

2023: Growth at all costs
2025: Efficient growth

Metrics investors kept asking about:

1. CAC payback period

  • Want: <12 months
  • Acceptable: 18 months
  • Pass: 24+ months

2. Burn multiple

  • Excellent: <1.5x (burn $1.50 for every $1 revenue)
  • Good: 2x
  • Pass: 3x+

3. Gross margins

  • SaaS: Need 70%+
  • AI companies: 50% acceptable (model costs)
  • Below 50%: Explain why

Quote from Sequoia:
“We learned from 2021. We’re not funding growth with terrible unit economics anymore.”

My Fundraising Experience (Real Talk)

My company:

  • AI-powered developer tools
  • $80K MRR
  • Growing 12% month over month
  • Team of 4
  • Burning $60K/month
  • 6 months runway

Goal: Raise $3M seed

Results after SF Tech Week:

  • Talked to 25 VCs
  • 3 interested in follow-up
  • 0 term sheets
  • Multiple “come back when you’re at $200K MRR”

The feedback:

  1. “Developer tools is crowded” (heard this 10 times)
  2. “Your growth rate is good but not exceptional”
  3. “Come back in 6 months”
  4. “We only do $5M+ rounds now” (this hurt)
  5. “How are you defensible vs GitHub Copilot?”

Reality check: I thought $80K MRR would be enough. It’s not.

The Alternative Funding Paths

What founders are doing when VC funding is hard:

1. Revenue-based financing

  • Pipe, Capchase, Lighter Capital
  • Get capital based on MRR
  • Pros: Fast, no dilution
  • Cons: Expensive (18-30% effective APR)

2. Angel syndicates

  • Smaller rounds ($500K-1M)
  • More friendly terms
  • Pros: Easier to close
  • Cons: Time-consuming (need 20-30 angels)

3. Strategic investors

  • Corporate venture arms
  • Industry players
  • Pros: Smart money, distribution
  • Cons: Slower, potential conflicts

4. Staying lean and profitable

  • Skip fundraising entirely
  • Bootstrap to profitability
  • Pros: Control, no dilution
  • Cons: Slower growth

Trend I’m seeing: More founders choosing option 4

The Bust Predictions

Timeline estimates from panels:

Optimistic (a16z):
“AI is real technology. Market will mature, not crash. Timeline: Gradual correction over 2-3 years.”

Pessimistic (hedge fund manager):
“When OpenAI or Anthropic misses revenue projections badly, dominoes fall. Timeline: 12-18 months.”

Realistic (YC partner):
“Some overvalued companies will fail. Real businesses will survive. The market will bifurcate.”

Comparison to dot-com:

  • Dot-com: Infrastructure wasn’t ready, revenue wasn’t there
  • AI now: Infrastructure is ready, but revenue isn’t scaling as fast as valuations

Key difference: AI is real technology (unlike pets.com)

But: 90% of AI startups will fail (like dot-com)

Advice I’m Taking to Heart

From founders who survived previous downturns:

1. Raise more than you think you need

  • Markets can stay shut for 18-24 months
  • Want 2 years runway minimum

2. Raise at sensible valuations

  • Down rounds kill momentum
  • Take the lower valuation if it means surviving

3. Focus on revenue, not hype

  • Revenue compounds, hype fades
  • Investors forget promises, remember numbers

4. Build something defensible

  • AI model improvements are commoditized
  • Need data, distribution, or network effects

5. Watch your burn

  • Default to profitability mindset
  • Growing 50% faster while burning 3x more isn’t worth it

6. Don’t assume the market stays hot

  • Have Plan B if funding dries up
  • Can you get to profitability on current runway?

The Uncomfortable Truth

My biggest takeaway from SF Tech Week:

The AI boom is real.
The AI funding bubble is also real.
Both things can be true.

Good AI companies will get funded.
Mediocre AI companies will die.
The difference is traction, differentiation, and timing.

For founders:

  • If you can raise now (and get reasonable terms), do it
  • If you can’t raise, focus on revenue
  • If you have 18 months runway, use it to get profitable

For investors:

  • The best deals are getting done quietly
  • FOMO investing leads to pain
  • Fundamentals matter again

Bottom line: We’re in the “trough of disillusionment” phase of AI. The survivors will build real businesses. The rest will be case studies in “what not to do.”

Anyone else fundraising right now? What are you seeing?

David :bar_chart:

SF Tech Week - Andreessen Horowitz, YC, Sequoia events

Sources:

  • Bloomberg “AI Funding 2025” (Oct 2025)
  • Bain & Co “AI Revenue Gap Analysis” (2025)
  • Yale SOM “AI Bubble Analysis” (Sept 2025)
  • Crunchbase Global VC Report Q3 2025

Adding the VC perspective from the other side of the table. I was at the same SF Tech Week events - here’s what we’re actually thinking. :briefcase:

My background: Partner at mid-size VC fund ($500M AUM), focused on enterprise/B2B

The Fundraising Market Reality

@product_david - your experience is unfortunately typical. Let me add context from our side.

Our fund in 2025:

  • Saw 2,400 pitches (Q1-Q3)
  • Took 180 meetings
  • Made 6 investments
  • Conversion rate: 0.25%

Compare to 2023:

  • Saw 1,800 pitches
  • Took 150 meetings
  • Made 12 investments
  • Conversion rate: 0.67%

We’re investing HALF as many companies while seeing MORE pitches.

Why We’re So Selective

Reason 1: The 2021 Hangover

Our 2021 investments:

  • Deployed $120M across 15 companies
  • Average valuation: 25x revenue
  • Thought process: “Growth at all costs, market is huge”

2025 status:

  • 8 companies: Down rounds or struggling to raise
  • 4 companies: Flat or modest up rounds
  • 3 companies: Actually doing well
  • Success rate: 20%

Our LP (limited partners) are PISSED.

Result: We can’t afford another 2021.

Reason 2: Portfolio Company Pressure

Current portfolio situation:

  • 40% of our portfolio companies need follow-on funding
  • Many are struggling to raise from other VCs
  • We need to reserve capital for “protect” rounds
  • Less money for new investments

This is true across the industry.

From LP perspective (shared at a16z event):

  • 2021-2022: VCs deployed aggressively
  • 2023-2024: Market correction
  • 2025: VCs need to support existing portfolio
  • New investment pace: Down 60%

Reason 3: Market Saturation

AI categories we’re seeing:

Developer tools: 350+ companies
Customer support AI: 200+ companies
Sales AI agents: 180+ companies
Legal AI: 120+ companies

Our thought process:
“Why invest in the 180th sales AI agent when we don’t know which 5 will survive?”

Strategy: Wait for market consolidation, then invest in winners at Series B.

What Actually Gets Funded

I’ll be honest about our investment criteria (2025):

MUST HAVES (non-negotiable):

1. Revenue traction

  • Seed: $50K+ MRR minimum
  • Series A: $1.5M+ ARR minimum
  • Growing 10%+ month over month

Why: Proves product-market fit exists

2. Strong unit economics

  • CAC payback <18 months
  • LTV/CAC ratio 3x+
  • Gross margins 60%+ (50%+ for AI infra)

Why: We learned from 2021 that growth without economics doesn’t work

3. Defensibility story

  • Proprietary data
  • Network effects
  • Unique distribution
  • Deep technical moat

Why: “Fine-tuned GPT-4” isn’t defensible

4. Proven team

  • Previous startup success
  • OR deep domain expertise
  • OR exceptional early traction

Why: First-time founders raising pre-traction is nearly impossible now

NICE TO HAVES:

  • Existing investors (signals validation)
  • Strong metrics (NRR 120%+, low churn)
  • Clear path to $100M ARR
  • Large, growing market

The Valuation Discussion

@founder_felix mentioned the valuation trap - this is REAL.

How we think about valuations now:

Seed (pre-$1M ARR):

  • 2023: $15-30M post-money (AI hype)
  • 2025: $8-15M post-money (back to fundamentals)
  • Correction: 50% down

Series A ($1-3M ARR):

  • 2023: $50-80M post-money
  • 2025: $30-50M post-money
  • Correction: 40% down

Why lower valuations are GOOD for founders:

Example:

Scenario A: High valuation

  • Raise $3M at $30M post ($10M/share implied)
  • 18 months later: $2M ARR, trying to raise Series A
  • Need $100M+ valuation to avoid down round
  • Market offers $60M (based on 30x revenue)
  • Down round or die

Scenario B: Reasonable valuation

  • Raise $3M at $15M post ($5M/share implied)
  • 18 months later: $2M ARR, trying to raise Series A
  • Need $50M+ valuation to avoid down round
  • Market offers $60M (based on 30x revenue)
  • Up round, everyone happy

The math matters.

What’s Working (Real Examples)

Companies we funded in 2025:

Company 1: Healthcare AI

  • What: AI for medical coding/billing
  • Why we invested:
    • $100K MRR at pitch
    • Healthcare has money and pain point is clear
    • 130% net revenue retention
    • Founder was former healthcare exec
  • Valuation: $12M post-money seed

Company 2: AI security tooling

  • What: Security testing for AI systems
  • Why we invested:
    • New category (not crowded)
    • 20 paying enterprise customers
    • $80K MRR, growing 20% monthly
    • Technical moat (PhD founders, novel approach)
  • Valuation: $18M post-money seed

Company 3: Vertical AI for manufacturing

  • What: AI for supply chain optimization
  • Why we invested:
    • Boring industry, real pain
    • Proprietary data from 10 years of consulting
    • $150K MRR at pitch
    • Clear path to $10M ARR (200 target customers identified)
  • Valuation: $25M post-money Series A

Pattern: Specific industry + proven traction + clear economics

The “AI Winter” Probability

From our internal analysis and LP conversations:

Bear case (30% probability):

  • OpenAI or major AI company misses revenue badly
  • Public market AI stocks crash (NVIDIA, etc)
  • Funding dries up for 12-24 months
  • Lots of companies die

Base case (50% probability):

  • Gradual correction over 2-3 years
  • Weaker companies fail to raise, die slowly
  • Strong companies keep getting funded
  • Bifurcated market

Bull case (20% probability):

  • AI revenue scales faster than expected
  • Killer apps emerge
  • Market stays hot
  • Valuations justified

My personal view: Base case

Why: AI is real technology (unlike dot-com vaporware), but 90% of current AI startups don’t have sustainable businesses.

Advice for Founders From VC Side

1. If you can raise at reasonable terms, do it NOW

Market could close quickly. We’ve seen this before:

  • 2008: Credit crisis, funding dried up overnight
  • 2022: Rate hikes, valuations crashed in 3 months

Don’t assume the window stays open.

2. Revenue > everything else

I saw a pitch at SPEEDRUN:

  • Beautiful demo
  • Impressive tech
  • No revenue

Pass.

Compare to:

  • Ugly demo
  • Simple tech
  • $100K MRR

Interested.

Revenue proves product-market fit. Nothing else does.

3. Ask VCs about fund dynamics

Questions to ask us:

  • When did you raise your fund? (New fund = more capital to deploy)
  • What’s your portfolio concentration? (Need reserves for existing companies?)
  • Have you invested in this space before? (Sector conflict?)
  • What’s your check size? (Can you lead the round?)

These questions tell you if we CAN invest, not just if we WANT to.

4. Be realistic about valuation

We passed on 5 companies in the last 6 months because founders insisted on 2023-era valuations.

Those companies:

  • 3 are still raising (9+ months, burning cash)
  • 1 did a down round at 50% of ask
  • 1 died

Lesson: Take the reasonable valuation and keep building.

5. Have a Plan B

Questions we ask ourselves:

  • Can this company get to profitability on current runway?
  • Do they have revenue-based financing options?
  • Can they cut burn dramatically if needed?

If the answer is “no, they need to raise or die” - we’re less likely to invest.

We want survivors, not companies dependent on continuous funding.

The Fund Economics Reality

Why VC math is broken right now:

Traditional VC model:

  • Invest in 30 companies
  • 20 fail (return 0x)
  • 8 return 1-3x
  • 2 return 10x+
  • Fund returns: 3-5x

Current reality (2021-2023 vintages):

  • Invested at peak valuations
  • Markdowns across portfolio
  • Very few exits
  • Fund returns: 0.8-1.5x (losing money)

Result: LPs (pension funds, endowments) are pulling back from VC

Data from LP conference:

  • VC commitments down 35% in 2025 vs 2023
  • Funds struggling to raise
  • Smaller fund sizes

Implication: Less money in ecosystem = fewer funded startups

What I’m Telling Portfolio Companies

Weekly partner meeting topics (real examples):

1. Extend runway

  • Cut burn 30-50%
  • Get to 18-24 months runway minimum
  • Assume fundraising takes 9 months (not 3)

2. Focus on profitability path

  • Show us you can get to break-even
  • Model it in detail
  • Make it believable

3. Improve unit economics

  • Raise prices (most companies underpriced)
  • Cut CAC (fewer expensive channels)
  • Reduce churn (this is 3x more valuable than new growth)

4. Prepare for difficult fundraise

  • Start 9 months before you need money
  • Talk to 100+ investors
  • Expect lower valuations
  • Consider alternatives (RBF, strategic investors)

The Opportunity

Controversial take: This is actually a GREAT time to start a company.

Why:

  • Less competition (tourists leaving)
  • Lower cost to build (AI tools for coding)
  • Customer budgets shifting (replacing humans with AI)
  • Talent available (layoffs from failed startups)

But: You need to build a REAL business, not a hype company.

Companies started in downturns:

  • Airbnb (2008 crisis)
  • Uber (2009)
  • WhatsApp (2009)
  • Slack (2009)

Pattern: Built during hard times, raised when they had proof.

My Prediction

18 months from now:

Dead:

  • Horizontal AI tools (too crowded)
  • “ChatGPT for X” companies (not defensible)
  • Companies that raised at crazy valuations and can’t deliver
  • Founder teams without domain expertise

Thriving:

  • Vertical AI in boring industries
  • AI infrastructure and tooling
  • Companies with proprietary data advantages
  • Efficient, profitable businesses

The market will consolidate 90%. The survivors will be worth billions.

@product_david - keep building. $80K MRR is actually good. Focus on getting to $200K MRR and profitability. Then fundraising becomes easier.

Fred :chart_increasing:

SF Tech Week - LP and VC events

Sources:

  • Pitchbook VC Deployment Data Q3 2025
  • National Venture Capital Association LP Survey 2025

Counter-perspective: I JUST closed a $4M seed round at SF Tech Week. Here’s exactly what worked. :rocket:

Background:

  • AI for customer support automation
  • Closed $4M seed at $20M post-money valuation
  • Led by top-tier VC
  • Took 4 months start to finish

Why My Raise Worked (When Others Failed)

Seeing a lot of struggle stories. Let me share what ACTUALLY worked:

Timeline:

Month 1 (June 2025):

  • Built investor list (150 VCs)
  • Warm intros through angels and advisors
  • Created detailed data room
  • Practiced pitch 50+ times

Month 2 (July 2025):

  • Sent 80 intro emails
  • Got 25 first meetings
  • 8 second meetings
  • 3 partner meetings

Month 3 (August 2025):

  • 2 term sheets
  • Negotiated terms
  • Diligence process

Month 4 (September 2025):

  • Closed at SF Tech Week
  • Multiple other VCs wanted to join

Key point: I OVER-PREPARED.

The Numbers That Mattered

What investors asked about (in order of importance):

1. Revenue and growth

  • $140K MRR at pitch
  • Growing 18% month over month for 6 months straight
  • Started year at $25K MRR

This was #1 topic in every conversation.

2. Unit economics

  • CAC: $8,000
  • LTV: $48,000 (based on 8% annual churn)
  • LTV/CAC: 6x
  • CAC payback: 11 months

Investors LOVED these numbers.

3. Market and competition

  • TAM: $15B (credible, bottoms-up analysis)
  • Direct competitors: 40+ (I was honest)
  • Our differentiation: Voice-to-voice AI (not just chat)

Honesty about competition built trust.

4. Team

  • Me: Former head of support at Series D startup
  • Co-founder: ML engineer from Google
  • 8 person team (mostly engineers)

Domain expertise was huge.

The Pitch That Worked

I watched 20+ pitches at SPEEDRUN that failed. Here’s what I did differently:

Bad pitch structure (what I saw):

  • Slide 1-5: Problem, solution, tech demo
  • Slide 6-10: Market size, competition
  • Slide 11-15: Team, ask

Problem: Gets to traction too late, loses attention

My pitch structure:

  • Slide 1: Hook (We save companies $500K/year in support costs)
  • Slide 2: Traction (Show the growth graph - revenue 6x in 9 months)
  • Slide 3: How (Voice AI for customer support)
  • Slide 4: Why now (Voice AI just got good enough)
  • Slide 5: Why us (Domain expertise + technical chops)
  • Slide 6: Market (TAM, how we’ll capture it)
  • Slide 7: Metrics deep dive
  • Slide 8: Ask and use of funds

Key: Traction FIRST. Everything else supports the traction story.

Feedback from VCs:
“Most founders bury their traction. You led with it. That’s why I took the meeting.”

The Questions That Got Me Funded

Questions investors asked that I nailed:

Q: “What happens when OpenAI launches voice support API?”

A: "They will. Our moat isn’t the model, it’s:

  1. Integration with support platforms (Zendesk, Intercom)
  2. Customer data for customization
  3. Human-in-the-loop workflow we built
  4. 18 months of domain expertise baked into product

OpenAI makes the core tech better, which helps us. We’re not competing with the model, we’re building the application layer."

This answer got me 2 term sheets.

Q: “Why can’t Zendesk or Intercom build this?”

A: "They can and they will. But:

  1. They’re 2-3 years behind (we’ve validated the market)
  2. They’ll acquire rather than build (we’re an acquisition target)
  3. Their AI features are generic, ours are specialized
  4. We’re growing 18% month over month - by the time they build it, we’ll have 500 customers and network effects"

Investors want to hear you’ve thought about existential risks.

Q: “What’s your burn and runway?”

A: "Burning $85K/month. $1.2M in bank. 14 months runway. But we’re prioritizing efficiency:

  • At current growth, we’re profitable in 18 months
  • This raise extends runway to 5+ years
  • We’re raising to accelerate, not to survive"

Framing matters. We’re not desperate, we’re accelerating.

The Due Diligence Process

What VCs actually checked:

1. Customer references (called 8 customers)

  • Verified satisfaction
  • Confirmed cost savings claims
  • Asked about our responsiveness

2. Financial audit

  • Reviewed all revenue (down to invoice level)
  • Checked for one-time deals vs recurring
  • Validated churn numbers

3. Technical review

  • Brought in external CTO to review code
  • Assessed technical team capabilities
  • Validated technical moat claims

4. Market research

  • Talked to industry experts
  • Analyzed competitive landscape
  • Validated TAM size

5. Background checks

  • Called previous employers
  • Checked with investors in our angel round
  • LinkedIn verification

This took 4 weeks. Be prepared.

The Term Sheet Negotiation

I got 2 term sheets. Here’s what I learned:

Term Sheet A (top-tier VC):

  • $4M at $20M post-money
  • 20% dilution
  • 1x liquidation preference (standard)
  • 2 board seats (them + me)
  • Pro-rata rights

Term Sheet B (mid-tier VC):

  • $4.5M at $22M post-money
  • 20% dilution
  • 1.5x liquidation preference (worse)
  • 2 board seats (them + me)
  • Full ratchet anti-dilution (much worse)

I chose A.

Why:

  • Better brand (helps future rounds)
  • Standard terms (won’t scare Series A investors)
  • Better support (portfolio resources)

$500K higher valuation wasn’t worth the worse terms.

Lesson from lawyer: “Always take the cleaner terms from better investors, even if valuation is lower.”

What I Did Differently (Key Takeaways)

1. Started with exceptional traction

$140K MRR isn’t normal for seed stage. We bootstrapped longer to get here.

Trade-off: Less dilution, better terms, easier raise

2. Nailed the story

Practiced pitch 50 times. Recorded myself. Got feedback from 10 advisors.

Most founders wing it. Don’t.

3. Knew my numbers cold

Every metric memorized:

  • MRR, ARR, growth rate
  • CAC, LTV, payback period
  • Churn, NRR, expansion rate
  • Burn, runway, unit economics

Investors asked unexpected questions. I had answers.

4. Built relationships early

Talked to investors 6 months before raising:

  • Sent monthly updates
  • Asked for advice
  • Built trust

By the time I raised, I wasn’t a cold pitch.

5. Created competition

Had multiple conversations happening simultaneously:

  • 8 VCs in diligence at same time
  • Created FOMO
  • Got better terms

Don’t do serial fundraising. Do parallel.

6. Had alternatives ready

  • Revenue-based financing term sheet as backup
  • Line of credit from bank
  • Angel syndicate ready to fill round

Never be desperate. Always have Plan B.

The Mistakes I Avoided

Watching other founders fail taught me:

Mistake 1: Raising too early

  • Saw founders raise at $20K MRR
  • They got terrible terms or no interest
  • Waited until $140K MRR - much easier

Mistake 2: Focusing on tech, not business

  • Too many founders pitch AI capabilities
  • Investors want to see revenue and customers
  • Led with business metrics, tech was secondary

Mistake 3: Inflated valuation expectations

  • Saw founders asking for 2023 valuations
  • They’re still raising 9 months later
  • Took realistic valuation, closed fast

Mistake 4: Weak financials

  • Many founders don’t track metrics well
  • Found discrepancies in diligence
  • We had clean books from day 1

Mistake 5: Solo fundraising

  • Trying to do everything yourself
  • I hired a fractional CFO to help
  • Worth every penny for financial modeling and diligence prep

My SF Tech Week Strategy

Why I closed at SF Tech Week:

Week before (preparation):

  • Scheduled 15 in-person meetings
  • Set up “office hours” at co-working space
  • Organized dinner with 5 VCs who were interested
  • Prepped updated deck with latest metrics

During SF Tech Week:

  • Monday-Wednesday: Back-to-back VC meetings
  • Wednesday evening: Investor dinner
  • Thursday: 2 term sheet verbal commitments
  • Friday: SPEEDRUN Demo Day (exposure)

The density of investors in one place = faster decisions.

Tactic that worked:

  • Told VCs “I’m meeting 10 other funds this week”
  • Created urgency
  • Got faster decisions

After SF Tech Week:

  • 2 weeks: Written term sheets
  • 2 weeks: Chose lead, negotiated
  • 2 weeks: Diligence
  • 1 week: Closed

Total time from SF Tech Week to closed: 7 weeks

For Founders Struggling to Raise

@product_david - you asked what’s working. Here’s my advice:

If you’re at $80K MRR:

Option 1: Raise now (realistic expectations)

  • Target $1.5-2M (not $3M)
  • Accept $10-12M valuation (not $20M+)
  • Focus on smaller funds and angels
  • Close faster, keep building

Option 2: Wait and grow

  • Get to $150K-200K MRR (4-6 months)
  • Raise $3-4M at $20M+ valuation
  • Better terms, more options

My take: Option 2 IF you have 12+ months runway

If you have <12 months runway:

  • Option 1 or revenue-based financing
  • Don’t die waiting for perfect round

What to focus on:

  • Growth rate (get to 15%+ month over month)
  • Unit economics (prove CAC payback <18 months)
  • Customer quality (logos investors recognize)

The Reality Check

Despite my success, I want to be clear:

I’m the exception, not the rule.

Stats from YC partners:

  • ~80% of seed stage companies struggle to raise
  • Average seed fundraise takes 6-9 months
  • Most don’t get their target valuation

Why I succeeded:

  • Right timing (caught investors between deals)
  • Right traction (above bar for current market)
  • Right preparation (over-indexed on quality)
  • Right story (domain expertise + metrics)
  • Some luck (investors liked voice AI space)

Don’t compare yourself to outliers. Focus on building a fundable business.

What I’m Doing With the $4M

Since everyone asks:

Team (60% = $2.4M):

  • 10 engineers (scale product)
  • 3 sales reps (grow revenue)
  • 1 customer success manager (reduce churn)

Marketing (20% = $800K):

  • Content marketing
  • Paid acquisition testing
  • Conference presence

Infrastructure (10% = $400K):

  • Model costs (will increase with volume)
  • Scaling systems

Buffer (10% = $400K):

  • Unexpected costs
  • Opportunities

Goal: Get to $1M MRR in 12 months, raise Series A

@product_david @finance_fred - happy to answer specific questions about my process!

Jenny :bullseye:

SF Tech Week - SPEEDRUN Demo Day participant

@finance_fred @sales_jenny - This thread is gold. Let me synthesize what I’m learning and adjust my strategy. :brain:

What I Got Wrong

1. My expectations were based on 2023 market

I thought $80K MRR would be enough because in 2023, that WAS enough.

Reality check from @finance_fred:

  • Conversion rates down 60%
  • Valuations down 40-50%
  • Bar for traction much higher

Adjustment: Stop being frustrated, adapt to current market

2. I focused too much on tech, not enough on business

My pitch spent 5 slides on AI capabilities, 2 slides on metrics.

Learning from @sales_jenny:

  • Lead with traction
  • Tech is table stakes
  • Business metrics win deals

Adjustment: Rebuild pitch, metrics first

3. I was impatient

Wanted to raise NOW because I’m at 6 months runway and panicking.

Wisdom from both of you:

  • Raising from panic position = bad terms
  • Better to cut burn, extend runway, raise from strength

Adjustment: I’m going to cut burn 40% and push fundraising to Q1 2026

My New Plan

Based on this thread, here’s what I’m doing:

Phase 1: Extend runway (next 2 weeks)

Current burn: $60K/month = 6 months runway

Cuts I’m making:

  • Cut 1 engineer ($12K/month saved)
  • Pause paid marketing ($8K/month saved)
  • Reduce cloud costs ($5K/month saved)
  • Cut tools and subscriptions ($3K/month saved)

New burn: $32K/month = 11 months runway

Why this works:

  • We’re not yet in scaling mode
  • Can still grow with current team
  • Buys time to improve metrics

Phase 2: Focus on metrics (next 4 months)

Current state:

  • $80K MRR
  • 12% month-over-month growth

Goal state (by Feb 2026):

  • $140K+ MRR (like @sales_jenny)
  • 15%+ month-over-month growth
  • CAC payback <18 months (need to calculate this properly)

How I’ll get there:

  • Double down on what’s working (PLG motion)
  • Kill what’s not (outbound sales isn’t working)
  • Improve onboarding (reduce time to value)

Phase 3: Prepare for fundraise (Jan-Feb 2026)

@sales_jenny’s preparation checklist I’m stealing:

  • Build investor list (150 VCs)
  • Get warm intros (leverage angels)
  • Create detailed data room
  • Practice pitch 50+ times
  • Clean up financials
  • Line up customer references

Phase 4: Raise (March-May 2026)

New realistic expectations:

  • Target: $2M (down from $3M)
  • Valuation: $12-15M post (down from $20M hope)
  • Timeline: 3-4 months
  • Backup: Revenue-based financing if needed

The Metrics I Need to Track

@investor_ian mentioned these, I’m now tracking:

Growth metrics:

  • MRR, ARR
  • Month-over-month growth rate
  • New MRR vs expansion vs churn

Unit economics:

  • CAC (I wasn’t tracking this properly)
  • LTV (need to fix churn tracking first)
  • CAC payback period
  • LTV/CAC ratio

Efficiency:

  • Burn multiple
  • Magic number (sales efficiency)
  • Rule of 40 (growth rate + profit margin)

Customer health:

  • Logo churn vs revenue churn
  • Net revenue retention
  • Expansion rate
  • Time to value

I’m building a proper metrics dashboard this week.

Questions for @finance_fred

If I execute this plan:

Q1: Is $140K MRR + 15% growth enough for $2M at $12-15M post?

Q2: Do I need to focus on any specific metrics beyond what I listed?

Q3: Is March 2026 a good time to raise, or should I wait until later in the year?

Q4: What’s the realistic timeline I should expect?

Questions for @sales_jenny

On your fundraising execution:

Q1: How did you get warm intros to 80 VCs? Did you use a specific strategy?

Q2: What was in your data room? Can you share a checklist?

Q3: How did you practice your pitch? Just recordings, or did you do mock pitches with advisors?

Q4: The “create competition” tactic - how did you coordinate timing to have 8 VCs in diligence simultaneously?

Q5: What’s your advice for a solo founder (I don’t have a co-founder) - does that hurt chances?

What I’m Telling My Team

Tomorrow’s all-hands:

The situation:
“Fundraising is harder than expected. The market has changed. We need to adapt.”

The plan:
“We’re cutting burn 40%, extending runway to 11 months. Focus is on revenue growth and unit economics. We’ll fundraise Q1 2026 when we’re stronger.”

The goal:
“Get to $140K MRR by Feb, raise $2M, scale the team back up.”

The reality:
“If we can’t raise, we need to be profitable. That means getting to $150K MRR while keeping burn low. It’s doable.”

Transparency builds trust. I’m not sugarcoating the challenge.

The Bigger Picture

This thread crystallized something for me:

I was chasing 2023 outcomes in a 2025 market.

The game has changed:

  • Investors are cautious (burned in 2021-2022)
  • Bar is higher (need more proof)
  • Capital is scarce (funds can’t deploy as much)
  • Valuations are rational (back to fundamentals)

But @sales_jenny proved it’s still possible.

The difference:

  • She had better traction ($140K vs $80K MRR)
  • She prepared better (50 pitch practices)
  • She had alternatives (RBF, angels)
  • She chose realistic valuation ($20M vs $30M asks I was hearing)

I can do all of those things.

Just need 4 more months to get there.

Alternative Scenarios I’m Modeling

Plan A (base case):

  • Grow to $140K MRR
  • Raise $2M at $12-15M post
  • Scale team and grow

Plan B (if fundraising fails):

  • Get to $150K MRR
  • Cut burn to $25K/month
  • Become profitable (barely)
  • Raise from strength later, or bootstrap

Plan C (if growth stalls):

  • Revenue-based financing ($500K-1M)
  • Expensive but non-dilutive
  • Buys time to figure out product-market fit

Plan D (worst case):

  • Sell to competitor or strategic
  • Team gets acqui-hired
  • I learn from failure and start next company

I’m not putting all eggs in the VC basket.

My SF Tech Week Lessons

Beyond fundraising, here’s what I learned:

1. Network matters
Met 50+ founders facing same challenges. Now I have a support system.

2. Transparency wins
Founders who were honest about struggles got better advice.

3. Market timing is real
You can’t force fundraising in a closed market. Adapt or die.

4. Focus on controllables
Can’t control VC sentiment. Can control revenue, burn, metrics.

5. Resilience is the game
Founders who survive downturns build the best companies.

This is hard, but it’s not impossible.

Thank You

@finance_fred - Your honesty about VC economics helped me understand the OTHER side of the table. I was frustrated with VCs, but now I see the pressure you’re under too.

@sales_jenny - Your playbook is exactly what I needed. I’m literally copying your approach.

This thread is going in my fundraising playbook. Hope it helps other founders too.

Anyone else in fundraising mode? What’s your strategy?

David :bar_chart:

Updated post-SF Tech Week reflections