Stephanie SimsCapital strategist, entrepreneurial advisor, author, board member
    Recommended Reading

    How to Raise

    For active fundraisers.

    For founders who've decided to raise outside capital. Get inside how VCs evaluate deals, build investor relationships over time, and run a tight fundraising process.

    Kyle Harrison

    Investing 101 2.0 · Substack newsletter (26K+ subscribers)

    Why listen

    Kyle is a General Partner at Contrary and has invested across five different firms — Kickstart Fund (seed), Index Ventures (venture classic), Coatue (crossover), and TCV (growth) before Contrary. That spectrum matters: he's seen how a deal looks at every stage from a $500K seed check to a pre-IPO crossover round.

    For research, he's interviewed 90+ VCs across 70+ firms about the mechanics of the asset class. His writing is what you'd want a thoughtful GP's IC memo to read like — frameworks for evaluating risk, calibrating fund-returner math, and being specific about what you actually believe. Reading him is the closest most founders will get to sitting on the other side of the table before they pitch.

    Start here

    • What Do You Have To Believe? (May 2026) — Marc Andreessen's "onion theory of risk," plus the pre-parade / pre-mortem exercise. Use both before your next pitch.
    • The Puritans of Venture Capital — Why some firms have stayed small ($200–500M funds) for decades while others have ballooned into capital agglomerators. Helps you understand who you're actually pitching and what their fund math demands.
    • Build What's Fundable — A direct read on the gap between "interesting business" and "venture-fundable business." If you're raising, this is the calibration check.

    Stephanie's take

    A very human VC who talks about what's actually real when it comes to raising. Kyle has a sharp read on where the VC market is moving and isn't afraid to share it. He has a strong point of view and believes in conviction — which, in my opinion, is a huge part of being successful as a founder.

    Best fit for founders raising their first round of institutional capital. Read him to understand how VCs really think and how different kinds of investors actually differ from each other (they are not all the same). If you're sticking with friends & family or angels for now, he's less directly useful at this stage — come back to him when you're ready for institutional money.

    Mark Suster

    Both Sides of the Table · Long-running blog · LinkedIn

    Why listen

    Mark is Managing Partner at Upfront Ventures, the largest VC firm in Southern California, and led investments in Ring, Bird, Invoca, ThredUp, and Nanit. Before becoming a VC in 2007, he founded and sold two software companies (Coral, acquired by Salesforce; BuildOnline, acquired by Sword Group) — so the "both sides" framing is literal.

    His blog is one of the few places you'll get a sitting GP openly documenting term sheets, board dynamics, fundraising tactics, and how investors actually decide. It's the most operationally useful blog for someone actively running a process. If Kyle gives you the worldview of a VC, Mark gives you the playbook.

    Start here

    • Invest in Lines, Not Dots — Why investors back people they've watched grow over time. Should change how you start building investor relationships before you need money.
    • Both Sides of the Table — full archive — Search for "Raising Venture Capital" series, term sheets, and board posts when you hit each new step in your process.

    Stephanie's take

    A former operator who became a VC — hence Both Sides of the Table — and that combination shows up in everything he writes. His content skews a bit older now, but the suggestions are deeply practical and he isn't afraid to share the "gory details" of how fundraising and investor relationships actually work.

    Good for founders raising institutional rounds, and a bit more accessible than Kyle at earlier stages too — including friends & family and angel rounds. The single piece I quote most often is Invest in Lines, Not Dots — the cleanest framing of traction I've ever read. Use it to shape how you build investor relationships over time, not just how you pitch them in a single meeting.

    Peter Walker

    Head of Insights, Carta · LinkedIn · Data Minute podcast & newsletter

    Why listen

    Peter runs the Insights team at Carta, the cap table platform that holds data on 29,000+ startups — which means he sits on the most comprehensive private-market dataset on the planet. He turns that data into clear, well-designed charts on round sizes, valuations, dilution, employee equity, and survival rates. 97K+ LinkedIn followers and 30K+ subscribers to his weekly Data Minute newsletter.

    While the rest of this list is people sharing opinions and frameworks, Peter is the data layer. Before you decide whether your $1.5M target on a $10M post is reasonable for your stage and sector — Peter has the chart. Use him to sanity-check what's actually market, not what your one investor friend told you over coffee.

    Start here

    Stephanie's take

    Peter has the latest data on what's actually happening in the VC market — average round sizes, average valuations, time to raise the next round, average equity at each round, and benchmarks for what advisors, early hires, and co-founders typically get. He's the place to go for the numbers behind every fundraising conversation.

    Best for anyone who needs a real benchmark — whether you're setting your round terms, figuring out what to offer your first hire, or reasoning about your dilution path through the next two rounds. Follow him on LinkedIn for the ongoing pulse, and reach for the Carta reports when you have a specific number to pin down.

    Also worth knowing

    Names and references that come up enough in venture conversations that you should be familiar with them — even if I'm not pointing you at their full body of work.

    Paul Graham

    Co-founder of Y Combinator and author of paulgraham.com — the canonical essay archive on building a venture-backable startup. How to Raise Money and Do Things That Don't Scale are the highest-leverage starting points. Worth being familiar with the highlights — these essays come up enough in fundraising conversations that being unfamiliar can read as a gap.

    Jason Lemkin

    Founder of SaaStr — the world's largest community of B2B SaaS founders, with 12,000+ at the SaaStr Annual conference each May. Built EchoSign (sold to Adobe in 2011) before turning to founder-side fundraising advice and B2B SaaS investing. Active on LinkedIn with daily posts on AI, fundraising, and the SaaS market. Worth following if your company is B2B SaaS specifically — he writes more practical fundraising content for SaaS founders than almost anyone.

    Sebastian Mallaby — The Power Law (2022)

    The most current and readable history of the venture capital asset class — covering the founding of Sequoia, Kleiner Perkins, Benchmark, and the rest, and how the modern industry took shape. If you're going to work with VCs, understanding where the industry came from and how it actually operates is foundational cultural literacy. Read once to understand the people you'll be pitching.

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