ITR #002: Your Fundraising Timeline, Nailed. (Part 2 of 2)

Welcome back to Into the Ring!

Firstly, a quick THANK YOU for all of your messages of support! It feels great to be able to reach even more folks on what I know is a tough journey to fundraising success.

I also wanted to share that my new website is live - I’d love to know your thoughts. Take a look 👀 and let me know!

UPDATE 🆕: This week, I’m writing to you on my return from a quick trip back to the US, spending time in San Francisco and LA. I’m blown away by the energy in SF right now. It was wonderful to connect with investors and founders, and I came away invigorated. (Shout out to Robin Lobo, founder of Lumian AI and fellow Harvard MBA cohort. His AI-focused newsletter is one I never miss. Sign up). LA - what can I say? I’m missing that sunshine already. And the tacos. And the theme parks! Honestly, it was a blast. 

I’m back in London and back with the second part of our opening series, How to Plan - and Time - Your Fundraise. Last time, we outlined the six essential steps for preparing your fundraise, including the what and why behind each. Catch up here if you missed that.

This week, I’m going to lay out a timeline to align with each of our steps, with advice on how to set the pace, and what to do if you have more or less time to prepare that you’d hoped. Let’s dive in. 👇

The Perfect Fundraising Timeline 👌

First things first: in an ideal world, you’ll begin your fundraising preparations a solid two to three months in advance of when you wish to kick off. In my experience, this is pretty much the perfect amount of time to get prepared.

Why? Founders often feel rushed or underprepared if they cut this time short, risking missed opportunities or preventable mistakes. The more time you spend preparing, the better positioned you’ll be to impress investors and handle tough questions.

More time available? Great! Use that to nurture your investor network, refine materials, and have exploratory coffee chats with VCs before you officially kick off. You won’t regret any additional time spent on building your confidence and finessing your approach.

Less time available? No problem. You can still succeed, but you’ll need to streamline the preparation process. I’ll share tips for compressing timelines without compromising your chances below. 

Let’s assume you’re working with a two to three month window. Here’s how I would break down that time for you.

Step One: Define Your Fundraising Contours

• Duration: Two weeks.

• Dependencies: None – this should always be your first step.

• What You’ll Be Doing:

  • Deciding how much capital to raise, your target valuation, the type of investors you want to bring in (VCs, angels, or a mix), and which terms work for you (SAFE, convertible note, equity, etc.).

  • Conducting research through conversations with other founders, startup lawyers, and friendly investors. Use resources like Crunchbase or AngelList to get a sense of market norms.

• Move On When: You have a clear target for your fundraise and understand your ideal outcome, including key terms and valuation expectations.

Step Two: Create Compelling Fundraising Materials

• Duration: 1.5 to two months.

• Dependencies: Defining your fundraising contours is critical before this step.

• What You’ll Be Doing:

  • Starting with your pitch deck, as this is often the first thing investors will see. This will take several rounds of revision, so don’t rush it. Work with a designer if needed to ensure it looks professional.

  • Assembling other data room materials depending on your stage—financial projections, product demos, team bios, and market analyses. If you’re raising a later-stage round, detailed financials and metrics will be required.

• Move On When: Your pitch deck and data room materials tell a clear, compelling story about why your startup is an exciting opportunity for investors.

Step Three: Develop a Robust Investor List and Reach Out Process

• Duration: Two months (this can overlap with other steps).

• Dependencies: You’ll need to have a strong understanding of your fundraising contours.

• What You’ll Be Doing:

  • Building a tiered list of 75-150 investors, categorizing them by relevance and priority.

  • Researching each investor’s focus areas and track record to make sure they align with your sector and stage.

  • Warming up intros via your network or plan your cold outreach strategy (be sure to personalize each email with relevant insights).

• Move On When: You have a well-researched, tiered investor list, along with a clear plan for reaching out and securing introductions.

Step Four: Prepare for Investor Conversations

• Duration: Two weeks.

• Dependencies: Your pitch deck should be near completion before this step.

• What You’ll Be Doing:

  • Rehearsing your pitch regularly—both on your own and with other founders or trusted advisors.

  • Practicing answering potential investor questions, especially on tricky topics like valuation, competitive landscape, and long-term strategy.

  • Move On When: You feel confident delivering your pitch and handling any curveballs from investors.

Step Five: Finalize Your Other Initiatives

• Duration: Variable, depending on your situation

• Dependencies: None—this can be done throughout the preparation process.

• What You’ll Be Doing: Tackling any remaining tasks that could impact your fundraise: applying to accelerators, updating your website and LinkedIn profile, and finalizing legal documents.

• Move On When: You’ve taken care of all critical side tasks that could disrupt your fundraise once investor conversations begin.

Step Six: Set Your Investor Kickoff Date

• Duration: One set date, followed by a two week kickoff window

• Dependencies: You should have completed the previous steps before starting this one.

• What You’ll Be Doing: Setting a date for when you’ll officially begin investor meetings. During the first two weeks, aim to pack in as many initial meetings as possible to create urgency and momentum.

• Move On When: You have a packed two-week schedule of investor meetings, creating a fast-moving, high-energy fundraise that pushes momentum forward.

I Only Have Six Weeks! 😬

Nothing’s perfect, and it doesn’t need to be. If you have a shorter timeline than you’d like, focus on these three things:

• Priority #1: Focus on your pitch deck. It might not be perfect, but it should clearly communicate your story and why your startup matters.

• Priority #2: Start warming up those intros as early as possible. Relationships take time to develop, and you’ll need momentum once you officially begin your outreach.

• Cut back on: Long research phases or overly polished materials. The key is to be ready to communicate your value clearly, not to have everything perfectly wrapped up.

I Have Some Time…😎

If you’re at the other end of the scale, and find yourself with six months or more to work with, great! Invest this time wisely with my recommendations:

• Build relationships early: Use the extra time to have exploratory coffee chats with potential investors and fellow founders. Building rapport before you officially raise can be a game-changer.

• Deepen your research: Spend more time understanding market trends, comparable valuations, and investor expectations in your space.

• Improve your business: If your current metrics make fundraising difficult, use the extra time to shore up your numbers or refine your product.

I’m going to be real with you - there is no such thing as the perfect fundraise. But whether you have three months or six weeks, some solid preparation, a robust structure and a realistic timeline will go a long way to fundraising success.

Still need help? Got questions that can’t wait? Set up a call with me today - you’re just a click away from the tools and strategies you need to get funded.

Every other week, I’ll be reaching out to my network to get their take on important questions on every aspect of fundraising. Got a question you’d like me to ask? Let me know. This week, I asked the million dollar question…

Q: How did you handle rejection from investors?

Thanks for stepping Into the Ring 🙏

Thank you for reading today, and for your support. If there’s anything that resonated with you, simply hit reply and let me know. Your time and attention is precious, and I want to share ONLY the most meaningful and actionable fundraising insights.

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