Stephanie SimsCapital strategist, entrepreneurial advisor, author, board member

    To Raise or Not to Raise

    For founders deciding whether to take on outside capital at all. The internet, the media, and a steady drumbeat of gurus push a funding fantasy - the assumption that every ambitious founder will (and should) raise venture capital. The reality is more nuanced. Most successful businesses are built without it; some thrive with it; and there's a whole middle ground that rarely gets talked about - angel-led structures (like Rand's $1.3M LLC round at SparkToro), single-investor private equity (like 37signals' minority stake from Jeff Bezos), debt financing, revenue-share funds, family money, and others. The voices in this section have lived both sides of the binary and can help you cut through the noise to figure out what's actually right for you.

    Is this right for you?

    Read this if:
    • You assume serious founders raise venture capital
    • Someone has told you that you need investors to be taken seriously
    • You're not sure whether equity, debt or customer revenue fits your business
    Go straight to another guide if:
    Foundations

    Chris Guillebeau - The Art of Non-Conformity

    Chris's body of work questions the defaults you've absorbed about what success and ambition should look like. Before you decide whether to raise outside capital, you need to be honest about what you actually want - not what you've been told to want. The Art of Non-Conformity is the right pre-decision read: it makes space for a path that fits you, not the path everyone assumes you'll take. About the book.

    DHH - RECONSIDER

    The clearest case ever made for choosing a profitable, sustainable software company over the unicorn-or-bust default. Plus the DHH vs Jason Calacanis debates on This Week in Startups for a direct head-to-head with a leading VC. Read it.

    Azevedo, Scheuer, Smetters & Yang - Dilution vs. Risk Taking

    The numbers behind the funding fantasy. These Wharton and University of Zurich economists tracked 157,669 VC-backed companies and 248,454 founders from 1987 to 2025, using SEC filings and data from PitchBook, CB Insights and others. They found that 88% of founders receive zero exit value, and that the top 1% capture 79% of the total. The paper's main question is how taxing unrealized capital gains would affect founders, but that one finding is the reality check to keep in mind before you treat venture as the default path. Read the paper.

    Other voices

    These three founders have taken outside capital, turned it down, or done both, and they write honestly about what each choice cost them. My take on each one is on the left; where to start reading is on the right.

    Rand Fishkin

    Co-founder, SparkToro · Previously CEO, Moz · Author of Lost and Founder · SparkToro blog

    My take

    Rand has built a different path that fits him. He has a clear idea of what makes sense for his goals and is pursuing funding that fits - instead of falling for the funding fantasy that VC is the one true path.

    And he's back in the game despite real setbacks. That kind of resiliency is exactly what founders need to see; it's a reminder that the choice you make today isn't permanent, and that there are paths beyond the binary you're usually told about.

    Start here
    • Lost and Founder (book) - Read this before you decide to raise venture capital. The most honest first-person account of what the VC path actually costs.
    • SparkToro Raised a Very Unusual Round of Funding - The funding announcement and the open-sourced documents. A concrete proof-of-concept that the third path exists.
    • SparkToro blog - His current writing home. Marketing, audience research, and ongoing reflection on the alternative-funded path.
    • Rand on Medium - Older long-form essays, including reflections on Moz and the VC experience.
    Why listen to Rand +

    Rand co-founded Moz, took $30M+ in venture capital, and became the public face of one of the most-watched marketing software companies of its era - before the journey ended with painful realizations about what the VC path had cost him personally and strategically. He documented all of it in Lost and Founder: A Painfully Honest Field Guide to the Startup World (2018) - the most candid first-person account of the VC experience you'll find.

    He then co-founded SparkToro in 2018 with a deliberately unusual funding model: $1.3M from 35 individual angels (no institutional VC), structured as an LLC so investors get profit distributions instead of waiting on an exit. He open-sourced the funding documents. SparkToro has been profitable every month since November 2020 and has already returned 100% of investor capital. It's a third path - not bootstrap, not VC - and Rand has been the most public, articulate advocate for it. He's the cleanest "lived both sides, has thought hard about the choice" voice on this list.

    Dharmesh Shah

    Co-founder & CTO, HubSpot · OnStartups blog · LinkedIn · agent.ai

    My take

    Dharmesh is a technical founder who's stayed deeply technical even while running a public company. He's very active in AI - building agent.ai alongside leading HubSpot - which gives him a current operator's view on how technology is reshaping the way businesses get built right now.

    His LinkedIn is particularly good on the latest technical approaches to improving operations, which is useful for any founder regardless of funding path. The broader body of work skews toward VC and rapid-growth thinking - keep that lens in mind. Best for founders leaning toward (or already on) the VC path who want to see how a technical founder reasons about building and scaling with capital.

    Start here
    Why listen to Dharmesh +

    Dharmesh sold his first company (Pyramid Digital Solutions, an IT services business) for a modest exit, then deliberately co-founded HubSpot in 2006 with a different plan: take on serious venture capital, build a category-defining company, and go public. HubSpot IPO'd in 2014 and is now worth tens of billions - and they raised across multiple market cycles along the way, giving him a long-arc insider's view of how VC dynamics shift over time.

    He's the cleanest mirror to Rand: lived both, chose VC the second time, and would do it again. He's been blogging at OnStartups for almost 20 years and still actively publishes on LinkedIn and his Connecting Dots newsletter on agent.ai. Reading him gives you the case for VC made by a founder who built a real business with it - not a pitch from someone selling the path.

    Greg Head

    Host of Practical Founders Podcast · CEO peer groups · LinkedIn

    My take

    Greg has been an operator inside a company that took a lot of money - and he's spent the latter part of his career supporting software founders looking for a different way to grow and sell their businesses. That dual perspective is rare, and it's part of why his content lands differently than someone who's only ever been on one side.

    Best for SaaS founders who believe there must be a better way to build what they want. He's a great fit if you're looking for success stories or examples of how others did it - and his Practical Founders community is worth a look if you want more than content (a peer group built specifically for this path). I had the opportunity to work with Greg when he was still in Phoenix, and he has a huge heart for supporting founders building the kind of business they want instead of what others expect.

    Start here
    Why listen to Greg +

    Greg is a 30-year software veteran (three companies, including a CRM IPO) who runs Practical Founders - a podcast and CEO peer group community focused specifically on founders building valuable software companies without big funding. The podcast features weekly interviews with serious founders who started, grew, and often sold their companies on their own terms; over 140 founders have been on the show, representing $11B+ of founder equity created.

    His angle is the antidote to the funding fantasy. Where most podcast and content feeds celebrate the founders who raised big and exited bigger, Greg specifically curates founders who proved you could build a great company another way. If you're working through whether to raise, his interview library is one of the deepest collections of "how I did it without big funding" stories anywhere.

    Caveat: His focus is primarily on SaaS founders, so the most useful interviews are software-flavored. Worth scanning his archive for founders in your specific industry.

    Also worth knowing

    Additional writers and posts worth pulling out as you work through the decision - some are featured elsewhere on this list, some live independently here.

    Jason Cohen - built one of each

    Cohen bootstrapped Smart Bear and raised $300M+ for WP Engine. The Bootstrapped Founder interview walks through the specific reasoning behind his decision to take VC for WP Engine after bootstrapping Smart Bear - exactly the "I chose this and here's why" articulation this section is built around. Plus his full archive for ongoing thinking.

    Alex Turnbull - chose bootstrap, twice

    Alex's first company was venture-backed and acquired; he turned down $12M and $5M VC offers for Groove and is deliberately bootstrapping again with Helply. Read his Journey to $100K series for the inside view of the choice.

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