What Jason Calacanis Asks on This Week in Startups: 50 Due Diligence Questions to Master

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This Week in Startups is famous for sharp, no-BS questions, and I hear founders ask all the time what Jason Calacanis is really looking for when he grills a pitch.

If you want to pass that test, you need to master due diligence questions before an investor ever opens your deck.

In this guide, I share the 50 due diligence questions I keep on my desk, the exact topics Jason hits repeatedly, and how I’d answer them in a live pitch.

You’ll see practical examples, common founder mistakes, and how to prep so demo day feels like a layup, not a firing squad.

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What Jason Calacanis Asks on This Week in Startups: 50 Due Diligence Questions to Master

1) Why Jason’s questions matter more than your deck

I’ve watched hundreds of founders overperform on slides and underperform in Q&A.

On This Week in Startups, the pitch rarely sinks you.

The follow-ups do.

Jason Calacanis questions are designed to find signal fast.

He compresses due diligence into 15 intense minutes.

He cares about three things.

Do you know your numbers.
Do you know your customer.
Do you know where the next 12 months of growth will come from.

If you can answer those clearly, the deck is a formality.

For more on building a crisp narrative under pressure, see our blog post: The 5-Slide Pitch That Wins First Meetings.

2) The 50 due diligence questions to master

I keep these questions as my rehearsal checklist.

They cover market, traction, economics, team, product, and process.

What problem are you solving in one sentence.
Who is your ideal customer profile (ICP) and how do they buy today.
What is your unique insight that incumbents missed.
What is your current monthly recurring revenue (MRR) or annual run rate (ARR).
What is your month-over-month growth for the last six months.
What is your gross margin today and your target at scale.
What is your customer acquisition cost (CAC) by channel.
What is your payback period on CAC.
What is your customer lifetime value (LTV) and the assumptions behind it.
What is your churn and net revenue retention (NRR).
What is your top-of-funnel source mix and conversion rates.
What is your average sales cycle and who is the decision-maker.
What is your win rate against the top three competitors.
What is your pricing model and where are you leaving money on the table.
What’s the hardest part of onboarding and how are you fixing it.
What usage metric best predicts retention.
What is your TAM, SAM, and SOM, and what bottoms-up data supports it.
What wedge gets you into the market fast.
What feature is your true moat and why it’s hard to copy.
What technical debt could bite you in the next 12 months.
What regulatory or compliance requirements apply (SOC 2, GDPR, HIPAA, etc.).
What is your burn rate and runway including and excluding new hires.
What are your top three hires and why now.
What roles are you over-leveled or under-leveled on.
What is your cap table and any SAFEs/notes with MFN or valuation caps.
What is the total raised to date and what milestones you achieved per dollar.
What is your use of proceeds for this round with milestone mapping.
What scares you most if growth doubles.
Where is your main bottleneck in the funnel today.
What cohort retention looks like by segment or plan.
What experiments moved the needle last quarter.
What will you kill this quarter to focus.
What channel do you believe is the next breakout and why.
What partnerships or integrations actually drive revenue.
What part of the product customers love versus tolerate.
What is your NPS and what you learned from detractors.
What top three customer objections and how you counter them.
What security posture and incident history you have.
What patents, IP, or data advantage you hold.
What your roadmap cuts look like if the round is only half filled.
What’s the one slide you’d bet the company on.
What’s your plan if a competitor clones your core feature next month.
What’s your biggest founder mistake so far and how you corrected it.
What’s your 10x plan to make the next 12 months non-linear.
What do early adopters do with your product that surprised you.
What is your ideal next investor and why they’re a fit.
What’s the exit logic if IPO is off the table.
What is the single metric that matters at this stage and why.
What’s your blunt answer to “Why now.”
What is the ask and how this check de-risks the company.

I recommend recording yourself answering each question in under 45 seconds.

If you can’t, you’re not ready for Jason.

3) Market sizing that doesn’t get eye-rolls

I don’t lead with a trillion-dollar TAM slide anymore.

I lead with how many target accounts exist and how many I can win this year.

Investors want bottoms-up math and customer proximity.

Count ICPs, not humans.
Use real deal sizes from your current pipeline.
Show path from wedge to expansion.

Example.

If I sell SOC 2 automation to 40,000 US SaaS companies with 2–500 employees, and my average contract value is $12k ARR, my near-term SAM is 40,000 x $12k = $480M.

I’ll target the 5,000 companies actively pursuing compliance this year.

That story lands.

For more on TAM/SAM/SOM, see our blog post: Practical Market Sizing for Seed and Series A.

4) Customer pain and validation beyond surveys

Jason loves hearing from customers directly.

I bring two live quotes and one screenshot.

Even better, a quick call-in.

Show wallet-on-the-table proof like paid pilots or LOIs.
Show before/after time saved or revenue gained.
Show what they used to do and why it broke.

Analogy.

If your product is painkiller, I should feel the headache on slide one and see the ibuprofen on slide two.

5) Traction that tells a story

Raw revenue is table stakes.

I pick a single “north star” metric that matters now.

Early stage: weekly active teams, activation rate, day-30 retention.
Mid stage: ACV, sales velocity, NRR, expansion revenue.
Late seed/Series A: payback period, gross margin trend, cohort curves.

Story beats spreadsheet.

Connect the metric to a decision you made and the next decision you’ll make.

6) Unit economics without squirming

Unit economics are where founders start hedging.

I keep it painfully simple.

CAC by channel, blended CAC, and payback in months.
Gross margin now, target at scale, and drivers to get there.
Contribution margin after variable costs.

If you don’t have clean cost allocations yet, say so.

Then outline how this round funds that hygiene.

For more on metrics hygiene, see our blog post: Startup Metrics That Matter: A Plain-English Guide.

7) Sales motion clarity beats bravado

I separate self-serve, product-led growth (PLG), and sales-led motions.

Mixing them confuses the model and the message.

PLG: activation, PQL thresholds, in-product upsell.
SMB sales: inbound SLAs, SDR quotas, demo-to-close.
Mid-market/enterprise: multi-threading, pilots, procurement steps.

If you say “we’re bottom-up and top-down,” show the org and funnel that support both.

Otherwise, pick one to dominate first.

8) Go-to-market that passes the “week” test

Jason often asks, “What can you do in a week to get 100 more customers.”

I like to show a one-week sprint that’s repeatable.

Spin up a targeted webinar with a partner.
Ship a mini-feature and announce to a niche Slack community.
Launch a “migration tool” that imports from a competitor.

If you can’t design a one-week win, your GTM might be too abstract.

For more on fast GTM loops, see our blog post: The 7-Day Growth Sprint Playbook.

9) Product roadmap investors can actually underwrite

I cut the roadmap into milestone-based chunks.

Milestone A (0–3 months): reliability, onboarding, analytics.
Milestone B (3–6 months): expansion features, admin, SSO.
Milestone C (6–12 months): ecosystem integrations, API, platform.

I tie each milestone to a revenue motion.

If a feature doesn’t move activation, expansion, or margin, it’s probably vanity.

10) Technical moat that isn’t hand-wavy

“We use AI” won’t cut it.

I define the moat in concrete assets.

Proprietary data flywheel or unique labeling pipeline.
Distribution lock-in via embedded workflows or file formats.
Switching costs through history, automations, or compliance.

If open source is the base, I explain our closed extensions and cloud advantage.

11) Team and founder–market fit

Jason often asks, “Why you.”

I answer with collisions between my past and the customer’s pain.

Jobs I’ve done that mirror the buyer’s day.
Systems I’ve built in this exact problem space.
Communities I can mobilize on day one.

If the team has gaps, I call them out and show concrete candidates or hiring pipelines.

12) Fundraising history and cap table cleanliness

Nothing kills momentum like a messy cap table.

I keep it clean and transparent.

Total raised to date, instruments used, and any special terms.
Current option pool and refresh plan.
Founder ownership post-round and control considerations.

If you have stacked SAFEs with different caps, prepare a cap table simulation under various raise sizes.

For more on cap table strategy, see our blog post: Cap Table Triage Before Your Next Round.

13) Use of proceeds with milestone math

“Hiring and growth” is not a plan.

I break the round into milestones with explicit cost and outcome.

$400k to grow activation from 22% to 35% via onboarding revamp.
$600k to stand up mid-market motion and close 20 pilots.
$300k to achieve SOC 2 Type II and unlock enterprise procurement.

Each block unlocks the next round’s story.

14) Competitive landscape without trash talk

I map competitors by buyer and use case, not logo soup.

I show what we ignore, what we go head-to-head on, and where we win.

Legacy suites: broad, slow, high switching cost.
Point tools: fast, narrow, integration tax.
New entrants: feature overlap, unclear wedge.

I include two respectful compliments and one surgical critique per competitor.

15) Regulatory, security, and risk posture

Security is a sales blocker if you don’t own it.

I keep a tight answer ready.

Compliance: SOC 2 roadmap, GDPR data flows, HIPAA scope if applicable.
Security: encryption, key management, incident response.
Privacy: data retention, deletion SLAs, subprocessor list.

Show the policy binder, not just the promise.

16) Data room readiness that shortens diligence

Jason’s team will ask for a data room if they lean in.

I pre-build it so I can share within an hour.

Company: charter, cap table, prior docs.
Finance: P&L, bank statements, ARR/MRR by cohort.
Product: architecture, roadmap, security docs.
GTM: pipeline, win/loss, churn reasons.
Legal: contracts, IP, privacy, DPA templates.

Label clearly, date everything, and keep a changelog.

For more on data rooms, see our blog post: Data Room Checklist That Closes Rounds.

17) Metrics hygiene and weekly reporting

I treat metrics like a product.

They need owners, SLAs, and QA.

One source of truth for ARR, MRR, churn, CAC, and cash.
Weekly dashboard with a one-line narrative.
Monthly deep dive with cohort and funnel diagnostics.

When numbers slip, I present the counterfactual plan before the investor asks.

18) Demo day strategy you can repeat

Demo day isn’t a performance.

It’s a process.

Open with the pain and your one-line fix.
Show the magic moment in the product in 30 seconds.
Click through your “money slide” and stop talking.

Post-demo, I send a one-page summary with three crisp asks and two calendar links.

Make it stupid-simple to say yes.

19) Founder mistakes I still see

I’ve made most of these.

No shame, just fixes.

Overcomplicating market size with vanity numbers.
Ignoring churn drivers until it’s too late.
Mixing PLG and enterprise without resourcing either.
Waiting to hire RevOps until Series A.
Raising without a milestone plan and burning for activity, not outcomes.

When you fix a mistake, say it out loud in the pitch.

It builds trust.

20) How I practice for Jason’s follow-ups

I use a simple loop.

Record a 10-minute pitch and 20-minute Q&A.
Transcribe with AI and highlight hedges, filler, and rambling.
Rewrite answers to fit 30–45 seconds with one number and one story.
Run a mock with a brutal friend who interrupts.

Practice to the point you can be interrupted mid-sentence and still land the plane.

For more on rehearsal tactics, see our blog post: Mock Pitch Framework: From Ramble to Precision.

Investor expectations: what changes by stage

Expectations shift fast from pre-seed to Series A.

I map answers to the stage I’m in.

Pre-seed: insight, speed, and first love from users.
Seed: activation, early revenue, repeatable acquisition.
Series A: cohort retention, payback, and path to margin.

Say the quiet part when you’re pre-everything.

Own uncertainty and show the test plan.

Pitch questions that win seconds back

On the podcast, time is oxygen.

I ask smart return-serve questions that move me forward.

“Would you like the 30-second version or the deep dive on CAC.”
“Do you want the bottoms-up TAM math or how we wedge in first.”
“Should I walk through the last cohort or the average across all.”

Guiding the dialog shows control without being combative.

Podcast insights I’ve applied in the wild

I’ve copied three tactics I heard founders use on This Week in Startups that worked for me.

Bring a live dashboard link so you can answer any metric question on-screen.
Offer a customer intro before they ask.
Give one contrarian belief and a test you’re running to prove it.

It signals readiness for diligence, not just theater.

Story arcs investors remember

Humans remember arcs, not spreadsheets.

I frame mine with a simple pattern.

Origin: the moment I felt the pain viscerally.
Breakthrough: the insight that cracked the problem.
Momentum: the three proof points that show compounding.
Ask: the capital that de-risks the next leap.

I avoid hero fiction and stick to receipts.

How to build the “money slide”

I design one slide that could sell the entire round.

It’s usually a cohort curve or payback trend.

Clear axes, no clutter.
Three annotations to tell the cause, not just the effect.
One sentence headline that says the quiet part.

When I share it, I stop talking for five seconds.

Silence lets the data punch.

Handling tough follow-ups without flinching

Tough questions aren’t attacks.

They’re shortcuts to conviction.

I use a simple three-step reply.

Agree with the risk.
Share the current evidence.
Describe the next test.

Example.

“You’re right, churn is high at 6% monthly in SMB.

We cut onboarding steps from 9 to 4 and saw day-30 retention lift 8 points in the last cohort.

Next, we’re rolling guided templates for the top three jobs-to-be-done, which we expect to lift activation by another 5 points.”

Pricing and packaging like a pro

Jason will pounce if your pricing looks random.

I ground it in value metrics and buyer psychology.

Pick a value metric that scales with customer outcomes.
Bundle to raise ACV but keep an entry plan as a wedge.
Run price tests every quarter and document results.

If you’re freemium, defend it with payback math, not vibes.

Hiring plan investors can underwrite

“We’ll hire great people” isn’t investable.

I show the recruiting pipeline and the scorecards.

Named advisors or candidates for critical roles.
30/60/90 plans tied to measurable outcomes.
Comp bands and equity philosophy to avoid over-dilution.

For more on building your hiring machine, see our blog post: First 10 GTM Hires: Sequencing and Scorecards.

Operating cadence after the check clears

Investors back habits.

I outline my operating cadence upfront.

Weekly exec meeting with three KPIs and one blocker.
Monthly board update with a one-page memo and dashboard.
Quarterly strategy review with roadmap reallocation.

Show the rhythm now and investors will trust the song later.

Your one-page diligence memo

I end every pitch with a one-page memo that makes diligence a yes-or-no decision.

Problem, solution, ICP in one paragraph.
Three proof points with links to evidence.
Unit economics snapshot.
Milestone plan with use of proceeds.
Data room link and calendar link.

It’s the bridge from show to substance.

FAQs

What if I don’t have revenue yet.

Focus on activation, retention, and usage intensity in a tight ICP, plus signed pilots or LOIs.

Investors back velocity of learning when revenue is early.

How do I answer a question I don’t know.

Say “I don’t know yet,” add what you’re testing this week, and promise an update with a date.

Credibility beats improvisation.

How much detail should I share on CAC if it’s still moving.

Share channel-level CAC with confidence intervals and what you’re doing to converge the numbers.

Moving is fine.

Hand-waving isn’t.

Should I bring live product or recorded demo.

Bring both.

Use a 30-second clip for reliability and keep a live build ready for follow-ups.

What if my TAM looks small.

Show a credible expansion path from wedge to adjacent jobs, and quantify the step-ups.

Small today is fine if expansion is durable.

Do I need SOC 2 before raising.

No, but a clear roadmap with dates, owners, and budget helps close enterprise-leaning investors.

What’s a good seed-stage payback period.

Under 12 months is strong for SMB and 12–24 months for mid-market, provided gross margins support scale.

How do I defend pricing in a price-sensitive market.

Anchor on outcomes, use good-better-best packaging, and show case studies where higher tiers create net savings.

What’s the best way to present churn.

Break it down by segment and reason, show cohorts, and outline targeted fixes with timelines.

Can I push back on a premise I think is wrong.

Yes.

Stay respectful, bring data, and propose a test to arbitrate the disagreement quickly.

Conclusion

Great pitches feel effortless because the hard work happened before the room.

When you master these 50 due diligence questions and frame your answers with precision, you’ll be ready for the fastball questions Jason Calacanis asks on This Week in Startups.

Build your question bank, rehearse under a clock, and make diligence a formality.

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