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Playbooks for raising capital and selling your company
108 articles from Jason Kirby. No theory, no fluff, just what works.
Post-Exit Mistakes Founders Make With Money, Risk & Mindset
Sriram Gollapalli sold iLab to Agilent, then spent years watching founders—including himself—make the same wealth mistakes. Here's what goes wrong after liquidity hits.
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How to Get in Front of Buyers Before You're for Sale
The best acquisitions start 18–30 months before the LOI, with a spreadsheet, a pilot, and zero intent to sell.
Build vs Buy: How Founders Should Think Like Corp Dev
Most founders are running product and corp dev simultaneously without realising it. Here's the framework to make that tension work in your favour.
How to Sell Your Startup When You're Low on Runway
A tactical playbook for founders with three months of cash and no time for the standard M&A process.
How Feature Bloat Kills Conversion, Retention, and Fundraising
Feature bloat rarely crashes your product — it just quietly erodes clarity, slows adoption, and kills your fundraising story one unused feature at a time.
Who Actually Buys Founder-Led Startups: Strategics, Rollups & PE
Most founders build toward a buyer that doesn't exist. Here's what strategics, rollups, and PE firms actually want — and what kills deals before they start.
Venture Orphans: How to Exit When Your VCs Have Moved On
If your investors have gone quiet and growth has plateaued, you may be a venture orphan — here's how to run a disciplined sell-side exit from that position.
Why Founders Should Hire an Investment Banker to Raise Capital
The "don't use a banker" default costs founders more than a fee ever would — in time, dilution, and terms left on the table.
Vibe Coding for Non-Technical Founders: Build, Demo, and Raise
AI-assisted "vibe coding" lets non-technical founders ship working MVPs without a dev team—here's how to build one investors will actually take seriously.
Hire People You Know Will Leave
Optimizing startup hiring around loyalty locks in clock-punchers. Hire future founders instead, and you'll get the ownership mindset you actually need.
Why "Quick" Fundraises Rarely Happen: A Realistic Timeline
Founders consistently underestimate how long a VC round takes. Here's what actually happens — and how to stop burning months on avoidable delays.
Why Investors Don't Fund Overworked Founders
Founders who raise capital protect their time ruthlessly — they're not filing 83(b)s or chasing payroll. Here's what separates the ones who close rounds from the ones who burn out.
What Actually Happens to Startups That Never IPO or Get Acquired
Most startups don't land a headline exit. Here's what the realistic outcomes look like—and how to plan for them before you hit a wall.
How to Build a Fundraising Narrative Investors Can't Ignore
A spreadsheet gets you a meeting. A story gets you a check. Here's how to build a fundraising narrative that makes investors feel FOMO about passing.
Equity, Debt, or M&A: Picking the Right Capital Strategy
Most founders default to VC because it's the loudest story in the headlines. Here's how to match your capital strategy to your actual business.
Women-Led Startups Outperform. The Funding Gap Persists.
Women founders generate better returns but receive just 2% of venture capital—a gap driven by access, bias, and network effects.
Due Diligence Mistakes That Kill Fundraising Deals
Investor interest doesn't close a round — surviving due diligence does. Here are the eight mistakes that kill deals after the pitch.
Reverse Engineering an Investor Pipeline That Closes
Most founders build their investor pipeline like a bad sales funnel—too many leads, no qualifiers, zero strategy. Here's how to fix that.
DeepSeek's $6M AI Model: What Founders Should Learn About Capital Efficiency
DeepSeek trained a model rivalling OpenAI's o1 for under $6M and wiped $560B from Nvidia's market cap — here's the disruption playbook founders should steal.
How to Decode and Handle the 15 Toughest VC Questions
Investors rarely say what they mean. Here's what 15 common VC questions actually signal—and exactly how to respond to each one.
Startup Trends VCs Are Betting On in 2025
A sector-by-sector breakdown of where venture capital is flowing, and what it means for founders deciding where to build and raise.
Founder Branding: Why Your Personal Narrative Moves Investors
If you're planning to raise capital in the next 6–9 months, building a personal brand isn't optional—it's your pitch deck in human form.
100 Newsletters In: What Starting Thunder Actually Taught Me
Jason Kirby reflects on why he built Thunder after a failed startup, what 400+ companies raising $1.2B+ looks like in practice, and what SAFE dilution data from Carta actually means for founders.
How to Raise Capital When Investors Are Tightening Belts
Funding winters don't stop great companies — but they do punish sloppy pitches, thin networks, and founders who haven't extended their runway.
5 Ways to Fund Your Startup Without Giving Up Equity
VC isn't your only capital option—and it might not be your best one. Here are five non-dilutive funding paths that let you keep full ownership.
The 12-Month Fundraising Plan Every Founder Should Follow
A month-by-month capital-raising roadmap—from first relationship to signed term sheet—so you never have to fundraise from desperation.
The Hustle Porn Trap: Grind Culture's Real Cost for Founders
Hustle culture romanticizes the 4 a.m. wake-up and the 120-hour week—but for most founders, it's a fast lane to burnout, not an empire.
Customers as Your Best Fundraising Tool: Turn Users Into Investor Proof
Your customer base is more persuasive than any pitch deck — here's how to systematically use their stories, data, and loyalty to close your next round.
How to Hire and Scale a Startup Team That Grows With You
Filling seats isn't the same as building a team. Here's how early-stage founders should think about hiring, culture, and leadership as they scale.
The Debt Sandwich: Why Stacking SAFEs Can Cost You 20% of Your Company
SAFEs are fast and founder-friendly — until you stack too many. Here's what the dilution math actually looks like, and why the structure eventually works against you.
When to Update Your Product: Four Signals Founders Ignore
Missing the right moment to update your product costs you users, team morale, and deals. Here are the four signals that tell you it's time.
Founder-Market Fit: Why Investors Bet on the Right Person
Product-market fit gets all the attention, but investors are really asking a harder question: are you the right founder to win this specific market?
Startup Equity Split: How to Divide Shares Fairly With Co-Founders
Equity splits set the power dynamics, motivation, and investor story for your entire company—here's how to get them right from day one.
How Non-AI Startups Can Still Win VC Funding
Nearly half of all US VC dollars have flowed to AI startups. Here's how founders without an AI play can still carve out their slice of the remaining pie.
Are You Too Broke for Venture Capital? What Founders Must Know
Personal financial runway matters as much as company runway — and wealthier founders have structural advantages most VCs won't admit out loud.
Why VCs Pass on Your Startup — and How to Fix It
Investors don't pass on bad ideas — they pass on bad timing. Here's what momentum actually means and how to manufacture it before you pitch.
The 4 Metrics Every Founder Must Track to Survive and Scale
Four reporting models—revenue, cash burn, cohort retention, and acquisition funnel—tell you everything about whether your business will survive the next 12 months.
How Much Should Founders Pay Themselves?
A stage-by-stage framework for founder salaries—from zero at launch to market rate at scale—with one cautionary tale that shows what goes wrong when you get greedy too early.
Do You Love the Problem You're Solving? A Founder's Litmus Test
Passion for your problem—not your solution—is what separates fundable founders from those who waste years building the wrong thing.
Questions Every Founder Should Ask VCs Before Taking Their Money
Most founders pitch hard and listen passively. The ones who close better deals flip the script — interrogating investors before any term sheet appears.
Choosing Between a VC Firm's Brand and the Partner
When two term sheets look equal on paper, the firm's brand versus the partner's relationship can make or break your next 7–10 years.
Why You're Struggling to Raise Venture Capital
Most founders chasing VC have a growth, retention, or market problem — not a pitch problem. Here's how to diagnose which one is killing your raise.
Founder-Led Sales: Why You Must Sell Before Hiring a Sales Leader
Most early-stage VCs won't back a founder who can't sell. Here's why doing it yourself first is the only path to sustainable revenue—and a hirable sales team.
When SAFEs Aren't Safe: What Every Founder Must Know
SAFEs are fast and founder-friendly, but they carry real risks that are pushing VCs toward convertible notes. Here's what you're actually signing.
How Much Should a Startup Raise? Finding the Right Number
Raising too much or too little can kill a startup. Here's a practical framework for finding the optimal funding amount at any early stage.
Do You Need a Co-Founder? Data, Trade-offs, and Equity Splits
The numbers strongly favor founding teams, but solo founders can win too — here's how to decide, find a partner, and split equity fairly.
How to Run a Board Meeting That Actually Helps You Build
Most early-stage founders dread board meetings. Here's how to reframe them as a strategic tool — and run one that actually moves your company forward.
How to Choose Startup Advisors (and Avoid Equity-Hungry Charlatans)
Most startup advisors are a waste of equity. Here's a battle-tested framework for finding ones who actually earn their stake.
No, Your Market Isn't That Big: TAM, SAM, SOM Done Right
Most founders inflate their market size and lose investor trust. Here's the framework to calculate TAM, SAM, and SOM numbers that actually hold up.
Corporate Transparency Act: What Every Founder Must File
Congress's anti-money-laundering law now requires most startups to report ownership to the government — or face $500/day in fines and potential jail time.
Startup Equity Compensation: Stock Options, RSUs, and How to Structure Them
Early-stage startups can't outbid Big Tech on salary — here's how to use stock options and RSUs to attract talent, align incentives, and keep your cap table clean.
Liquidation Preferences: What the Trados Case Teaches Founders
Trados sold for $60M and common shareholders got nothing. Here's how liquidation preferences work and how to negotiate them before it's too late.
Investor Updates: How to Stay in Touch and Raise Smarter
Consistent, well-structured investor updates are one of the cheapest insurance policies a founder can buy — here's exactly how to write them.
6 Venture Capital Books Every Founder Should Read Before Raising
Six books that explain VC mechanics, term sheet traps, and the founder-investor relationship—chosen for operators, not analysts.
What Carta's Trust Crisis Teaches Every Founder
When Carta killed a core revenue line overnight to protect customer trust, it handed founders a masterclass in damage control—and a blueprint for building trust from day one.
Language-Market Fit: Why Your Customers Don't Understand You
Product-market fit means nothing if your words don't land. Here's how to close the gap between what you sell and what customers actually hear.
Why Your Startup Should Launch a Newsletter
A newsletter keeps your company top-of-mind for investors and clients — and the content, format, and consistency lessons that make it actually work.
How to Get a Warm Intro to VCs (and Why Cold Email Fails)
Sending hundreds of cold emails to investors is a red flag, not a strategy. Here's how VCs actually evaluate your outreach — and how to get the intro that opens the door.
Why Founders Shouldn't Fear Down Rounds
A down round isn't a death sentence — it's a market correction. Here's what the data says, and how to think about it clearly.
What Unicorn Founders Actually Have in Common
An Endeavor study of 200 unicorn founders demolishes the Harvard-dropout-to-billions narrative — here's what the data actually shows.
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