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- Within Startup Guide: Fundraising for Purpose-Led Founders (Part 1)
Within Startup Guide: Fundraising for Purpose-Led Founders (Part 1)
The Outer Work

Love it or hate, obtaining external funding is often a key part of growth for many startups.
And fundraising is tactical and strategic, but it’s also energetic in nature.
If you’re currently fundraising or considering it, this two-part guide will make your life easier by arming you with the ins and outs of a fundraising process AND sharing the personal development tools that will help you cultivate the energy that will make your actions more successful.
WHAT WE’LL COVER
PART:1 THE OUTER WORK
Manifesting a successful fundraise
Why It Works
How to Manifest
Visualization for Fundraising
Expanders & Mentors
Building Unshakeable Confidence in the Face of No’s
Why Showing Yourself the Evidence Works
Daily Journaling
List of Praises & Success
How to Deal with a No
Changing Your Fundraising Story
The Work of Byron Katie
Your Nervous System’s Role in Fundraising
Tapping Into Your Intuition
Protecting your Time and Energy
Working with a Coach While Fundraising
👋 HI, I’M ROSLYN
I’m an executive coach and founder at Within, where I help purpose-led founders scale their impact without burning out.
Prior to Within, I co-founded The GIST, a women-run sports media brand making sports more inclusive, accessible and fun for underserved sports fans. While there, I was recognized as Forbes 30u30 in their media category and accelerated and funded by global brands like Facebook, Comcast NBC, Techstars and Billie Jean King’s Trailblazer program.
As the former Head of Finance, Ops & Growth, I raised $2.5m for the company from a variety of sources — from grants, loans and accelerators to SAFEs, convertible notes and an equity round.
Ultimately I ended up burning out from my company and had to transition out, which is a whole other story. But that event motivated me to want to support founders in building outstanding companies with more fulfillment, ease and connection to themselves.
While I’m here to share all the tactical advice around fundraising, I’m even more passionate about sharing what I wish I knew on the inner work side of things that would have made fundraising less overwhelming and more successful.
If you want to approach your fundraising round with more magnetism, self-assuredness and effectiveness, this guide is for you.
By the way, if you want tactical AND personal development advice on all types of startup topics beyond fundraising, you can sign up for the Within Newsletter and follow me on Instagram and LinkedIn.
The Outer Work
SHOULD I FUNDRAISE OR NOT?
While the media makes it seem like fundraising is a prerequisite to startup success, in reality only about 5 in 10,000 startups receive venture funding (less than 0.05%).
In startup culture, we’ve come to view raising capital as the goal we’re working towards, when in reality, building a profitable, lasting business business should be our goal, with fundraising merely as a tool to support that goal.
And many startups are actually a much better fit for bootstrapping or choosing an alternative funding source to venture capital.
Venture capitalists (VC’s) are typically looking for companies with high growth potential and a clear path to significant returns. More specifically…
WHAT VC’S ARE LOOKING FOR:
1. Massive Market Potential
TAM (Total Addressable Market) usually in the hundreds of million or billions.
Scalable across geographies or sectors.
2. Scalability
Business model that scales quickly and efficiently with tech or automation.
High gross margins and low marginal costs.
3. Traction
Early revenue, fast-growing user base, or strong engagement metrics.
Proof of demand (waitlists, paid pilots, viral growth).
4. Compelling Team
Founders with domain expertise and execution chops.
Ideally a technical cofounder or product-savvy team.
5. Clear Exit Potential
Acquirable or IPO-able.
Operating in a space with past VC wins or recent M&A activity.
If this isn’t you (or you don’t know yet if this is the type of company you want to build), that’s completely fine. In either case, you’re actually usually better off delaying outside funding as long as possible anyways. The longer you build independently, the more equity and control you retain.
Some of the strongest companies are the ones that prove they can thrive without venture capital because it forces them to get creative and solve problems that having extra capital can sometimes cover up.
And consequently, the more you build a thriving, profitable business that doesn’t need funding but merely wants it to accelerate what’s already going well, the better position you’ll be in to get demand from investors and obtain favorable investment terms.
If you’re not 100% certain VC is right for you at this moment, but your business would benefit from some additional capital, there are lots of alternatives to VC available to you, which we’ll get into shortly.
For now I’ve summarized some of the tradeoffs of raising VC.
PROS AND CONS OF RAISING VC, FOR PURPOSE-LED FOUNDERS:
✅ Pros of Raising Venture Capital | ⚠️ Cons of Raising Venture Capital |
1. Large Amounts of Capital Access to millions of dollars to grow fast. Useful for hiring, product development, go-to-market, or entering new markets. 2. Accelerated Growth VCs expect speed—so you’ll build, launch, and scale quicker than most bootstrapped peers. 3. Credibility & Visibility Being backed by a known VC can open doors: media, partnerships, top-tier hires, more funding. 4. Strategic Support Many VCs bring expertise, mentorship, and connections (especially if they’ve built or backed similar companies). 5. Risk Sharing You’re not taking on personal debt—if the business fails, it’s the VC’s loss too. | 1. Dilution of Ownership You give up equity (and control) with each round. Founders can end up minority shareholders in their own company. 2. Pressure to Scale Fast “Grow or die” mindset. If you're not growing hyper-fast, you're at risk of being cut off. May not align with your personal goals or mission. 3. Exit Expectations VCs need big returns—often pushing for an IPO or acquisition, whether or not that’s your ideal path. 4. Loss of Control Investors often join your board and may influence key decisions—sometimes at odds with your vision. 5. Time-Consuming Fundraising Raising a round can take 3–6+ months and distracts from building the actual business. |
QUESTIONS TO CONSIDER ON WHETHER VENTURE BACKING IS RIGHT FOR YOU
1. 🧭 Is my mission compatible with hypergrowth?
Will scaling fast amplify my impact or compromise it?
VCs want rapid, exponential growth. If growth would force shortcuts that undermine your mission or values (e.g., ethics, sustainability, inclusion), that’s a red flag.
2. 🤝 Do I want to give up control?
Am I ready to share decision-making power with investors who may not share my priorities?
VCs become part-owners and often board members. Even supportive ones have a say—and their north star is ROI, not always your purpose.
3. 🧨 Am I building a VC-backable business model?
Does my business have the potential to return 10x+?
VCs fund models that can dominate markets. If your venture has a steady impact but more moderate returns, alternative funding may be a better fit.
4. 🌱 What’s my definition of success?
Do I want to build to exit or build to last? How does either fit into my vision for my life?
VCs typically expect a liquidity event (sale or IPO) within 5–10 years. If your dream is long-term sustainability, VC might conflict with your timeline.
5. 💡 What would I do differently if I didn’t need to raise money?
Could I test, grow, or monetize in a way that keeps me aligned and in control?
Sometimes the assumption that funding = progress blocks creativity. Removing that pressure can spark more authentic, sustainable growth strategies.
TALK TO OTHER FOUNDERS
In addition to weighing the pros and cons and doing research, I would also highly recommend talking to variety of founders that have gone through different funding approaches:
The founders where VC has worked well for them
The founders that regret raising VC
The founders that have bootstrapped their growth
The founders that have used alternative funding like debt, crowdfunding or grants
Listen to what their experiences have been like, and notice what resonates and makes you feel curious, inspired and lit up.
And also notice what makes you contract or feel like you want to back away.
(You can also listen to founder stories on podcasts like Female Founder World or Found, but someone will likely be more candid with you 1:1).
TYPES OF FUNDING AVAILABLE TO YOU
If you don’t feel VC is for you, there are plenty of other options available. While they might not come with the news headlines, in many cases they can be a much better fit for your goals.
NON-VC FUNDING OPTIONS
1. Bootstrapping
Build with your own funds, reinvest revenue.
✅ Total control, no dilution.
⚠️ Slower growth, high personal financial risk.
2. Friends & Family
Early seed money from people who believe in you.
✅ Lower pressure, early support from your network.
⚠️ Risk of strained relationships if things go south.
3. Accelerators & Incubators
Programs like Y Combinator, Techstars, Antler, Entrepreneur First, and 500 Startups
✅ Small investment + mentorship + visibility + community.
⚠️ Competitive, and equity is often exchanged for a small check.
4. Grants & Competitions
Non-dilutive capital from governments, foundations, or pitch contests.
✅ Free money + sometimes recognition.
⚠️ Time-consuming applications, often restricted by eligibility or purpose.
5. Crowdfunding
Platforms like Kickstarter, Indiegogo, or equity-based ones like Wefunder.
✅ Builds community and validates demand.
⚠️ Requires strong marketing effort and fulfillment logistics.
6. Revenue-Based Financing
Repay a percentage of monthly revenue until a cap is hit (e.g. Clearco).
✅ No equity dilution, flexible repayment tied to growth.
⚠️ Not ideal for early-stage or pre-revenue businesses.
7. Angel Investors
Wealthy individuals who invest before or alongside VC.
✅ More flexible and aligned than institutional VCs.
⚠️ Still involves equity dilution and expectation of returns.
8. Loans & Debt Financing
Traditional bank loans, SBA loans, lines of credit, or venture debt.
✅ No equity loss; good for businesses with predictable cash flow.
⚠️ Requires personal or business credit, and you’re on the hook for repayment—regardless of success.
MY EXPERIENCE WITH STARTUP FUNDING
When I was co-leading The GIST, we were pretty scrappy with funding because we weren’t sure if we wanted to go the VC route. As a result we used ALL of the above funding sources (with the exception of revenue-based financing and crowd-funding).
In our earliest days, we did pitch competitions, raised with friends, family & angel investors and took part in a few different incubators and accelerators, including Techstars. At that point our media audience was in the <10,000 range, but the engagement and excitement for the brand was strong, we had a lot of conviction around the problem we were solving and the growth of the space we were in (which was a good bet! Women’s sports are growing fast).
We didn’t feel we were fully a fit for institutional VC (or maybe it was that they didn’t think we were a fit for them — we did pitch some and got lots of no’s!). We were also conservative about wanting to maintain control of our company, especially as a mission-driven business, so we relied on angel investors to raise some early capital (about $400k before heading into Techstars, who invested $120k, and then we raised an additional ~$200k coming out of the program from additional angels).
This was incredibly helpful for us because we were pre-revenue at that point and needed to build out an audience to a certain size in order to be able to start monetizing it with brand partnerships. So those early funding sources allowed us to build out our offering, hire an early team (and eventually start paying ourselves!), and grow our audience.
Once we grew our audience and were able to start monetizing it at a 5-figure monthly revenue, we were then able to raise a $1M equity round (about a year later), again with mainly angel investors (including repeat investors from the earlier round). At this point, we also took on a $300k loan from a bank (the BDC, a bank that supports innovation and technology in Canada) to supplement the raise. (Often banks, especially venture banks, are willing to fund companies at the same time or right after they raise an equity round.)
We applied for government grants that specifically fund innovation (again in Canada — with the National Research Council) which covered technical salaries and expenses related to building custom innovative technology for The GIST. We also found grants in Canada that funded wages for interns. Grants can be a bit of a pain to apply and maintain reporting for, but since they’re non-dilutive, it can absolutely be worth the time.
Finally, we received an additional $0.5M as part of our participation in a women in sports focused accelerator called Trailblazer, which is backed by Billie Jean King Enterprises, RGA and a venture firm — this was our only true traditional venture capital check.
I share my personal experience to illustrate that there’s no one right way to fund your startup. Everyone will have a different path based on their needs, preferences, timing and the type of company they’re building.
Know what your options are, talk to other founders about their experiences, and listen to your intuition.
SAFES VS CONVERTIBLE NOTES VS EQUITY ROUNDS
The last thing I want to get into on the investment vehicles front is the difference between SAFEs, convertible notes and equity rounds.
It’s quite common in earlier fundraising stages to use a SAFE or convertible note for simplicity and also because it might be too early to know what the startup should be valued at. SAFEs and convertibles defer the valuation until a later priced round.
At The GIST, we raised our pre-seed round on a SAFE and then did a priced round for our seed. Convertible notes were used with the accelerators we took part in.
Comparison
🧾 1. Convertible Notes | 🪙 2. SAFE (Simple Agreement for Future Equity) | 💰 3. Priced Round (Equity Round) | |
💡 What it is: | A loan that converts into equity in a future financing round (usually at a discount or with a valuation cap). | An agreement to give future equity without being a loan—no interest or maturity date. | A formal sale of shares in the company at a fixed valuation—investors get equity right away. |
⚙️ Key Features: | Has interest (like a loan). Has a maturity date (deadline to convert or repay). Converts into shares at next equity round. | Created by Y Combinator. Can include valuation cap and/or discount. Converts into shares during a future priced round. | Requires setting a valuation. Includes term sheet, legal docs, and possibly a board seat. Establishes a post-money cap table. |
✅ Pros: | Familiar structure for investors. Often includes both valuation cap and discount, giving early investors upside. Fast to execute and avoids setting valuation now. | Founder-friendly: no debt, no repayment pressure. Simple, fast, and cheap to issue. No valuation negotiation needed upfront. | Clean ownership structure—no future conversions. Sets a clear market valuation. Signals maturity to future investors |
⚠️ Cons: | Debt on your books until it converts. Maturity dates create pressure. Can get complex if not converted by the deadline. | Investors might hesitate if they prefer traditional notes. Too many SAFEs with varying terms can create cap table chaos later. No control over when it converts—can remain outstanding for years. | Legal process is expensive and time-consuming (lawyers, due diligence). Dilution is immediate. More investor rights (e.g., pro rata, board seats) may be required. |
If you do decide to pursue venture capital, I highly recommend the book Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist by Brad Feld and Jason Mendelson, to deeply understand how venture capital firms operate and what the terms of investment mean (especially in equity rounds).
If you’re going to be giving away a piece of your company (it’s a big decision!), you’ll want to be fully informed and educated on the implications at a detailed level.
HOW TO RUN A FUNDRAISING PROCESS
Okay, now that you have a better sense of whether or not and how you might want to raise external funding, let’s get into how to actually do it.
This part of the guide is targeted towards founders who are raising with traditional investors like venture capital or angel investors.
1. BUILD RELATIONSHIPS AHEAD OF TIME
If you anticipate you’ll want to raise capital at some point, it’s very powerful to be able to go into your raise with pre-existing relationships with investors, other founders and mentors in your space.
Go to founder/investor networking events, befriend other entrepreneurs, join communities, consider an incubator or accelerator, anything to start to build your network in the startup space. Nurture those relationships, ask for feedback on your startup, and build real human connections with people.
If you meet an investor or mentor you connect with and that seems willing to give you feedback or support you, add them to a monthly mentor email.
Your monthly mentor email should share your progress on your main KPI’s, your wins, challenges, and any asks from your mentors. Sending a consistent mentor update email showing progress and also honesty about challenges, builds trust with the network of mentors and investors you’re building.
2. CLARIFY YOUR “WHY” AND “WHAT FOR?”
Get clear on why you’re raising capital. What will the capital unlock? You should be able to answer what milestones you’ll be able to hit with the capital (as opposed to what the capital will be spent on).
✅ Examples of milestones:
Build MVP + get first 500 customers
Grow from $100k to $1.5M ARR
Expand into new markets
❌ Examples of spend (not a clear why for raising):
Hire a CTO
Spend on marketing and growth
Build out a sales team
Your financial model (which I’ll get into below) should show how you’ll spend the money you’re raising, in order to hit the milestone you’re raising for.
It’s hugely important to not only be able to tell the story of your company and how it solves a real problem, but also to convey what capital will allow you to accomplish and how that positions you for further growth.
3. CREATE A CLEAR, COMPELLING, CONCISE PITCH DECK
Your pitch deck should convey your company’s story, using hard numbers to back it up. It should ultimately get people excited about the opportunity and provide a starting point for the conversation and questions from investors.
Keep it short and sweet — assume someone will spend only 5 minutes reading your deck — what are the key takeaways you want them to leave with and the feeling you want to evoke? Try for 10-12 slides max with any supporting slides (for Q&A) in the appendix.
Before you get into the nitty gritty, plan out the structure of the deck. Think about the story you want to tell and how that story should flow. Order the main components of the deck accordingly.
For each slide, consider, if someone were to spend a few seconds skimming this slide, what is the main point I want them to take away from it? Consider writing that as a subtitle on the slide.
Make the deck visual. Don’t underestimate the power of design and use charts, graphics, logos and imagery where you can to convey or support takeaways.
Consider having a deck for sending ahead of time and a separate deck you present. The deck you send will need to be more detailed. The deck you present can be more simple and visual and you can speak to the details in real life.
Write a script for your pitch. Each slide should be a couple sentences. Think about the most important insights you want someone to take away from a slide and say that as simply as you can. It can be tempting to want to go into detail and show off your expertise, but it’s better to get your points across simply and clearly, maintain the story arc and their excitement, and leave getting into the details for the Q&A.
Send your deck to your network of mentors, founders and friendly investors. Practice pitching with them if they’re open to it. Get feedback and iterate on your deck and your pitch before officially kicking off your process.
In terms of the content of your deck, you should tailor it for the stage you’re fundraising at.
PITCH DECK COMPONENTS BY STAGE
Component | Pre-Seed | Seed | Series A | Series B |
Purpose | Selling the founder, vision and early insights - even if the product is still an idea | Selling the validation and momentum as you raise to find product-market fit (PMF) or early growth. | Focus on scalability and strategy. You’ve found PMF and now are looking for funding to scale: hiring, sales, marketing and infrastructure | Selling growth and operational excellence. You’re scaling and ready to dominate your category or expand. |
Problem | Clear articulation of the problem you're solving validated through early user feedback | Validated through early user feedback | Still relevant ”how big and urgent is it? | Reframed as company mission/impact |
Solution | MVP | Working product with strong signs of PMF | Refined product with strong usage | Mature product with strong moat |
Market Size/Opportunity | Big enough TAM to be VC-backable | Refined with some traction data | Large and proven with early wedge | Global or adjacent expansion plans |
Product / Demo | Concept, wireframes, or prototype | Screenshots or live demo | Live product, performance insights | Product roadmap + technical moat |
Traction | Early usage | Usage and revenue metrics | MRR/ARR, churn, retention, growth | Strong growth + retention cohorts |
Business Model | How you'll make money, pricing, LTV/CAC if known | Pricing, LTV/CAC | Detailed model with unit economics | Scaled model, CAC payback period |
Go-to-Market Strategy | Plans to acquire users / what channels are being tested | What channels are working | Working playbook + funnel metrics | Proven GTM engine |
Competitive Landscape | Basic landscape with your differentiator | More detailed analysis of players | Positioning + defensibility | Defensibility, IP, barriers to entry |
Team | Why you're the right team | Key hires and strengths | Team + planned hires for scale | Leadership team, hiring plan |
Customer Case Studies / Logos | Optional but nice to have | Early case studies — logos & testimonials | Valuable logos, testimonials | Proof of market adoption |
Financials / Metrics | Basic projections, burn rate | Metrics + projections + runway | Full financial model + KPIs | Full financial model + KPIs |
Use of Funds / The Ask | How much you’re raising and what for | Clear ask tied to growth plans | Precise ask with clear ROI | Growth-focused use of funds |
Vision / Roadmap | Product vision and market potential, short-term roadmap to PMF | Vision to scale | Vision to scale and expand | Big vision with multi-year plan |
PITCH DECK INSPIRATION
If you’d like to check out some real pitch decks startups have used to successfully raise for inspiration, you can go to Pitch Deck Hunt.
You can filter by stage and category to find a company similar to yours.
Ultimately, these are great to look at for inspiration but don’t copy anything slide for slide. Your pitch deck will be better if it uniquely suits what you’re building and the story you’re telling.
4. PREPARE YOUR MATERIALS
In addition to your pitch deck, you should have the following ready going into your fundraise process.
FINANCIAL MODEL
A financial model isn’t just about numbers — it should tell a story about how your business makes money, spends it, and grows.
Keep it simple and use formulas
Tell a story — growth should be logical and milestones should align with your raise
Plan for 3-5 years
A strong financial model includes:
An assumption tab, which may include:
Growth rates, pricing and monetization, hiring plan and salaries, marketing spend and CAC (customer acquisition cost), customer lifetime & LTV (Lifetime Value)
Revenue forecast
How do you make money?
Breakdown by revenue stream
Cost of goods sold (COGS)
What does it cost you to deliver the product?
Operating expenses (OPEX)
What are your core operating costs? (e.g. marketing & sales, HR, general & admin)
Hiring plan
Who are you hiring and when?
Profit & Loss Statement (P&L or income statement)
Your income statement: Revenue - COGS = Gross Profit - OPEX = EBITDA - interest, taxes, depreciation, amortization = Net Income
Cash Flow Forecast
How much cash do you need—and when?
Starting cash + Cash in (revenue, investment) - Cash out (expenses) = Ending cash balance
KPI’s Dashboard
Quick snapshot of key metrics (KPI = Key Performance Indicator)
Note: this is considered a full financial model. The expectation may be for something more basic for an earlier stage of fundraising (e.g. pre-seed), and more built out for a much later stage.
INVESTOR Q&A DOCUMENT
Prepare for your investor meetings by anticipating the questions they will ask and have solid, thought-out answers for them.
Here’s a great list written by Alex Iskold (investor at 2048 Ventures) that you can use to prepare.
I’ve included the questions below but the linked article itself shares exactly what investors want to know and how you can prepare for each question.
Who are your customers, and what problem are you solving for them?
What is unique about your solution? What is your unique insight?
How does your product actually work?
What are your KPIs? How do you measure growth? How do you know you have product/market fit?
What is your traction to date?
What is the size of this opportunity/total addressable market?
What are your CAC and LTV?
What is your business model?
How did you come up with your pricing?
What are your unit economics?
What is your go-to-market strategy?
What are your customer acquisition and distribution channels?
Why now?
Why you? What is your Founder/Market Fit?
Where did you grow up? Where did you go to school and work before?
How did you meet your co-founders?
Who are your competitors and how are you different?
What is your vision, your true North?
What milestones will you achieve with this financing?
How much will you be burning in a month?
What will be your MoM growth in customers and revenue?
When will you be profitable?
Why is your business defensible?
What is your intellectual property?
What is your tech stack?
What are the key risks in your business?
Who is the natural acquirer for your business?
How much capital did you raise so far, and on what terms?
Who are your existing investors?
How much capital are you raising and what are the terms?
DATA ROOM
When you get to the due diligence stage with an investor, they may request additional materials to support what you’ve shared through your pitch deck or investor meetings. What they’ll ask to see will vary depending on the stage you’re at.
Best Practices
Use Google Drive, Dropbox, DocSend, or Notion (VCs love easy access)
Organize into folders by category
Label files clearly: 2025_Financial_Model_v3, Deck_SeedRound_Jan25, etc.
Keep it read-only, update as needed
DATA ROOM REQUIREMENTS BY STAGE
✅ Likely required
🟡 May be requested
Category | Pre-Seed | Seed | Series A | Series B |
Pitch Deck | ✅ | ✅ | ✅ | ✅ |
Executive Summary / One-Pager | ✅ | ✅ | ✅ | ✅ |
Founding Team Info | ✅ | ✅ | ✅ | ✅ |
Problem / Solution Brief (deep dive beyond deck) | ✅ | ✅ | ✅ | ✅ |
Product Demo / Screenshots (video, screenshots, or access) | ✅ | ✅ | ✅ | ✅ |
Cap Table | ✅ | ✅ | ✅ | ✅ |
Fundraising Details (how much you're raising, SAFE/note terms if applicable) | ✅ | ✅ | ✅ | ✅ |
Market Research | 🟡 | 🟡 | ✅ | ✅ |
Customer Discovery Insights | 🟡 | 🟡 | ✅ | ✅ |
Financial Model | 🟡 | ✅ | ✅ | ✅ |
Product Roadmap | 🟡 | 🟡 | ✅ | ✅ |
Incorporation Docs | 🟡 | ✅ | ✅ | ✅ |
Advisors / Org Chart | 🟡 | 🟡 | ✅ | ✅ |
KPI Dashboard | ✅ | ✅ | ✅ | |
Customer/User Growth Data | ✅ | ✅ | ✅ | |
Legal Docs | ✅ | ✅ | ✅ | |
Go-to-Market Plan | ✅ | ✅ | ✅ | |
Tech Overview / Stack | ✅ | ✅ | ✅ | |
Customer Contracts / Testimonials | 🟡 | ✅ | ✅ | |
Board Materials | 🟡 | ✅ | ✅ | |
Data Privacy / Compliance | 🟡 | ✅ | ✅ | |
Hiring Plan / Org Chart | ✅ | ✅ | ||
Audited Financials / Clean P&L | ✅ | ✅ | ||
Customer Metrics (Cohorts, Churn) | ✅ | ✅ | ||
Sales Funnel Performance | ✅ | ✅ | ||
IP Filings / Strategy | ✅ | ✅ | ||
Security Policies | 🟡 | ✅ | ||
Performance vs. Plan | 🟡 | ✅ | ||
Board Decks / Investor Updates | 🟡 | ✅ | ||
Segmented Key Metrics | 🟡 | ✅ | ||
Enterprise-Grade Financial Controls | 🟡 | ✅ | ||
Legal Compliance Docs | 🟡 | |||
M&A Strategy / Market Map | 🟡 | |||
ISO / SOC Compliance | 🟡 | |||
Fundraising History with Terms | 🟡 |
INVESTOR INSIGHT
Something that is core to a successful fundraise is the balance of optimism and “realism”.
Do the “outer work” on the realism side and “inner work” on the optimism side. You need to bring both to a successful fundraise.
Being overly optimistic and not considering all the possibilities and risks can seem naive. And being overly realistic can seem pessimistic. And frankly, all the best startup ideas are not super realistic. They’re a risky shot at building something, a product that's part of a better future. And they’re never all going to work and that's okay.
To balance that as a founder, ahead of time, do the realism work and think about “What could go wrong?”, “How are we going to address that in our plan?” or “What are the risks we are going to accept as part of the business idea?” And be thoughtful about it — write an FAQ or a memo for yourself, address certain questions like that in your deck, in a data room or in a long-form email to investors to show them it’s something you thought through.
Get all that out of your system, put it on paper and be thoughtful, be organized about it.
And then allow yourself to show up to the pitch with your most energetic, positive and optimistic side. Because you’ve already done the work on the realistic side, you don't have to caveat your vision, your pitch, your vision. Just let the best positive version of your startup and vision shine through. Give yourself the permission to be bold, think big and to accept risk as part of the business.
By the way, if you’re finding this guide helpful and want more tactical startup advice like this you can sign up for the Within newsletter.
5. BUILD YOUR INVESTOR PIPELINE
I recommend using a spreadsheet to keep track of two parts of the fundraising process:
At the building pipeline stage, your focus is on identifying the right investors by researching, talking to other founders and compiling a list of investors that would be a fit based on the stage they invest at and categories they focus on.
By the way, this part of the process will likely take a decent investment of time if you’re starting from scratch. Fundraising is a volume game. To set yourself up for success, and to keep the momentum going, try to build a long list of potential investors you feel would be a fit early on.
Consider what industries they invest in, whether they have any similar (but not directly competing) companies in their portfolio, what stage they typically invest at and what check size they typically provide. All of these can be indicators of whether an investor is a fit for you.
You can set up your first tab of the spreadsheet with the following columns. (You can copy my template here).

At the same time you can set up the second tab of the spreadsheet to monitor ongoing interactions, using the following columns. (Again you can copy my template)

6. LINE UP WARM INTROS
If you’re able to, finding a warm intro to an investor will be more powerful than cold outreach. Some funds do welcome cold outreach (they may have a link or email on their website or LinkedIn profile), which is a good backup and you can absolutely try that. But a referral or warm intro usually goes a much longer way.
Here’s how:
Use your network of founders, mentors and advisors.
Once you have your investor pipeline that you’ve researched, use LinkedIn to see if you have any mutual connections with a potential investor.
Send a personalized, forwardable intro request to each connector (to make it incredibly easy on the person connecting you).
I learned about forwardable emails from Techstars, and specifically Alex Iskold’s blog. He says a forwardable email should include:
Introduction: Your name and name of your company, including URL
Business: 2-3 sentences about your business & why it’s interesting
Traction: 1-2 sentences about your traction / customers you have / progress you made.
Why: Looking for feedback
Ask: Could we do a quick 15 min call?
Here’s a forwardable email template.
7. TIME YOUR OUTREACH STRATEGICALLY
Once you’re feeling good with your fundraising materials, you’ve built out an extensive investor pipeline with potential warm intros and you’ve practiced and gotten feedback on your pitch, you’re ready to start your outreach.
You’ll want to try to schedule your meetings within a bound timeframe in order to build momentum.
Try reaching out to investors within a tight 2-3 week window
You can also stagger by tier. For example, schedule your top investor picks last, so that you can practice with the ones that are lower stakes, and hopefully you can let top investors know you already have a certain amount of capital committed by the time you speak with them (which can help show demand / create FOMO).
8. PITCH & FOLLOW UP
The experience of pitching investors will vary by investor. Some will want you to walk through your pitch deck and ask questions along the way. Others may have been through your pitch deck and will want to jump into asking you questions. Figure out which style you’re more comfortable with and try to lead with however you feel most confident.
At the same time, you’ll want to be flexible based on the context and vibe of the investor you’re pitching. For instance, if it’s a friendly early coffee chat it will likely feel more like a conversation. If you’re pitching to the firm partners later in the process, a more formal pitch will be more appropriate. Practice both walking through your deck and answers to your Q&A extensively so you feel confident and natural in either context.
Refine your pitch through live practice and continue to iterate your pitch and Q&A based on feedback and questions
Log your conversations in the investor pipeline and follow up within 24-48 hours.
Address common concerns proactively
Send over any requested information in a timely manner
Refer to the “Inner Work” section for how to manage your presence, anxiety and confidence going into these meetings.
A NOTE ON AUTHENTICITY WHEN PITCHING
Your pitch, your story, your interactions with investors and your leadership more broadly will be more successful if they are grounded in authenticity. It’s tempting to try and emulate founders that have been successful, but authentic passion is way more magnetic than perfection. Speak from the heart about why you’re passionate about your vision and how you’re building it in a way that’s unique to you.
FOUNDER INSIGHT
I absolutely loved this advice from Tracy Lawrence on this topic:
I learned almost too late in my Series A the value of showing up as my full, heartfelt self. As a female founder, I thought I had to wear a masculine mask—wearing brown Converse, mirroring the warlike language of male peers, muting the soul of what I was building. But all that posturing drained the life from my pitch.
What I was actually building was a love culture—one rooted in the intimacy of sharing food. And it wasn’t until my 29th pitch that I finally let myself show up as me. I spoke from the heart and let my passion lead. That’s when we closed the round.
Fundraising is vulnerable and high-stakes, and it can feel like there’s no room for you. But your authentic energy is your superpower. Trust it. Embody it. That’s what people invest in.
9. CREATE FOMO (ETHICALLY)
Convey to investors that things are moving quickly and that you have strong interest (if this is the case)
Use traction and term sheet conversations to build urgency.
Share updates (wins, commitments) without being pushy.
If an investor is not getting back to you, you can follow up with “If we don’t hear back from you, we’ll assume you’re no longer interested in this round”, which will prompt them to give you a more clear indication of if they’re truly still interested or just passively following along to see if other investors jump on the opportunity.
10. NEGOTIATE TERMS AND CLOSE
Through your investor meetings, ideally you’ll find an investor who is open to leading your round. This means they put in the largest check and set the terms for the round, and the rest of the investors “follow” (aka invest on those terms as well with smaller checks). In some stages (seed onwards) a lead investor might also ask for a board seat.
Review term sheets carefully and get legal review — especially if it’s more complicated than a SAFE.
Lean on your founder friends and mentors if you have questions or want a gut check on if the terms of investment are typically seen in the market.
Read Venture Deals by Brad Feld and Jason Mendelson to get an in-depth understanding of various venture terms like valuation, liquidation preferences and anti-dilution.
The round isn’t closed until the money is in the bank. Don’t stop scheduling new meetings and moving investors through the pipeline until the paperwork is signed and the money is in the bank. Unfortunately sometimes investors will soft commit and pull out, and you want to ensure that you are keeping the pipeline full in case this happens.
When you close, wow huge congrats and exhale! Take a moment to pause and celebrate this massive accomplishment!
Soak it up. Take a break, take a weekend away, allow yourself to decompress and your nervous system to regulate before you jump back into building mode. You’ll feel more clarity on how you want to proceed with your new capital if you allow yourself some stillness, rest and reflection after such a huge undertaking.
PROTECTING YOUR TIME & ENERGY
Fundraising can feel all-consuming, especially for first-time founders or solo founders. It can be easy to fall into a reactive loop, letting investor meetings, follow-ups and pitch prep take over your schedule and energy.
Here are a few ideas for helping you stay in your power, protect your focus and avoid burnout while fundraising:
1. Get Clear on Your Priorities During Your Fundraise
Fundraising is a huge undertaking so you’re not going to be able to do everything you were doing before AND fundraise at the same time. If you’re expecting to be able to do so, you’re setting yourself up for failure in both areas, and to be disappointed in yourself (which can lead to burn out).
Instead give yourself grace. What are the things that absolutely must continue to get done and what else can fall away or be postponed until after the raise? Get ruthless here.
2. Set Yourself and Your Team Up for Success
If you know your team is going to have to step up to fill in for you, set them up for success ahead of time.
Make the priorities and expectations abundantly clear. What are their goals? What does success look like? How is it being measured? Who is accountable for what outcomes?
Arm them with additional information they can use to make decisions without you. Clearly document or create videos (Loom is great for this) explaining processes they’ll need to carry out. Give them what they need to figure things out without having to ask you.
Empower your team — this is an opportunity for them to step up and grow.
If you don’t have a team to delegate to, take some time before your fundraise to see how you might be able to automate, outsource, postpone or eliminate tasks entirely.
3. Design Your Ideal Calendar and Stick to It
Ahead of time, decide what windows of time you’ll dedicate to fundraising activities (outreach, pitch prep, updating materials, etc.).
Outside of those blocks, protect time for attending your business’ needs, team management and rest.
Aim to schedule investor calls in set windows (e.g. 10am-2pm on Tuesdays-Thursdays), allowing you to stay in “pitch mode” and avoiding context switching.
4. Set Boundaries
Use tools like Calendly to set windows when specific groups of people can book time with you (e.g. investors for certain windows, team members for other windows).
Set your slack to Do Not Disturb and add a note to say when you will be available to answer slacks (e.g. I’ll be online to answer Slack messages from 11am-12pm and 3-4pm weekdays).
Block specific times in your calendar to attend to things like emails and don’t get distracted with these things outside of those blocks.
Know that you can always reschedule meetings or say no if you’re feeling overwhelmed or something/someone doesn’t feel aligned.
5. Schedule Time for Rest and Stillness
Fundraising can dysregulate your nervous system and rest and recovery will help you stay grounded, sharp and emotionally resilient.
Block off time for workouts, walks, therapy/coaching, journaling, nervous system practices, getting outdoors and anything that allow your brain to turn off.
Remember, your nervous system feeling safe and resourced is what will allow you to show up as the version of yourself that will be successful. It’s not selfish to slow down and take care of your nervous system - it’s a requirement for your success.
FOUNDER INSIGHT
We learned so much over four fundraising rounds. Our first friends and family round took five months to close $135K; our next round closed in just two weeks at $1.4M! In total, we've raised around $6M. The biggest lesson? Fundraising has to be your #1 focus while you're raising. Clear your calendar - no meetings, no social plans - so you’re fully available for follow-ups and new investor intros (we were on calls sometimes from 8AM until 11PM EST).
Make sure you also have a strong deck. As founders, you're so deep in the day-to-day that it can help to work with a deck designer to tighten your numbers and sharpen your story, since they're more removed from the business.
Finally, organization is critical. Keep a detailed tracker of every contact, including their probability of investing, cheque size, and when you last followed up. Once someone commits, don’t hesitate to check in daily until their funds are wired. It’s not glamorous, but staying on top of it makes all the difference in closing your round.
Thank you for reading and head over to Part 2 of this guide which will cover the Inner Work that will support your fundraise.
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