How to Raise Millions — And Why the Story Matters More Than the Numbers
9 questions every pitch deck (and founder) must nail
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We are thrilled to feature a guest post by Adam Wray, the founder and CEO of AstrumU. Before launching AstrumU in 2017, Adam was the CEO and president of Basho Technologies. Prior to that, he co-founded Tier 3, which raised $18.5M and was acquired by CenturyLink for just under $200M. In total, Adam has raised over $200M across angel, series A, B, and C rounds for his own companies and as an advisor to others.
If you have ever been curious about how to ask for millions and actually get it, you are in for a treat. Adam breaks down his 9 steps to raise money:
The Challenge: What Problem are you Solving
The Solution: What is Your Unique Approach
TAM: Total Addressable Market (T-Shirt Size It)
The MVP: What Are We Building (and What Will We Learn)
GTM Strategy: How Will You Make Money
Forecast: How Quickly Will This Scale
Competitors: Who Else is in the Game
The Team: Why You
The Ask: What Do You Need and What’s the Game Plan
Adam also unpacks what VCs are testing you on with their questions.
And if you want to go deeper, consider joining our new course - Raising Capital & Building a Business (starts Sept 20). You will get the inside look founders wish they had about starting a company, raising money, and building something that lasts. Adam will bring his many cycles of raising money, and I will bring my expertise on building a business, including how to get acquired and thrive through that process. Use code FOUNDERREADY at checkout for a 20% discount (expires August 14th).
How to Raise Millions — And Why the Story Matters More Than the Numbers
There’s a common misconception among first-time founders that raising capital is all about the numbers. If the spreadsheet looks good, the capital will follow. But ask anyone who’s raised serious money, and they’ll tell you the truth: investors don’t just buy into metrics, they buy into you. Your story, your conviction, and your clarity about the problem you're solving and why it needs to exist in the world.
I once raised a $1M pre-seed round with nothing but a PowerPoint, a story, and a clear pitch. No code. No co-founder. Just a tight deck that hit the 9 key beats every pitch needs to cover.
Here’s what every deck (and founder) needs to nail.
1. The Challenge: What Problem Are You Solving?
This is where every good story begins: the problem. If you skip past this, you’re missing the moment where the audience leans in and thinks, “Yes, that’s a real problem.”
To get this reaction, you need to frame the problem clearly. This isn’t a time to flex jargon or buzzwords. You want to explain the pain so that someone outside your industry gets it, and also in a way that builds urgency: Why now? What’s broken? What’s about to tip?
Make it human. Make it real.
Tip: If you can show the mission or impact, you make a large opportunity feel human. For example, when we framed our work around helping people measure their skills, it wasn’t just a tech play — it was about leveling the playing field for millions of learners and workers. That human story connected with investors, while the market potential — tapping into billions of dollars in economic opportunity — made it clear the impact could scale.
2. The Solution: What’s Your Unique Approach?
You’ve framed the problem — now, what’s your answer?
Here’s where you introduce your product or service as the obvious (and differentiated) solution. You don’t need to get too deep into the tech or the features yet. The key is to explain why this is the right solution, and why you are the right leader to build it.
Your goal is to show you understand the terrain deeply and that you've found a wedge others haven't.
Tip: Being “better” isn’t good enough. Be different and stand behind it.
3. TAM: Total Addressable Market (T-Shirt Size It)
Investors want to know the opportunity is big enough to matter — but “big” is relative. If you don’t have precise numbers yet, use the T-shirt sizing method. It’s a simple way to frame market size without losing credibility.
Here’s how I think about it, backed by what angels, early-stage VCs, and exit data actually show:
Size: Small
TAM Range: <$250M
How Investors See It: Often works for angels or small funds if there’s a clear expansion path into bigger adjacent markets. Harder to attract institutional VC unless you can “create” a bigger category.
Example Outcomes: Vertical SaaS for niche industries, B2B tools for specialized markets. E.g., Mindbody started as a wellness studio software niche before expanding.
Evidence & References: Wing VC: early-stage markets in “hundreds of millions” viable if expansion path exists. Most exits in this TAM are <$100M (PitchBook, 2024).
Size: Medium
TAM Range: $250M–$1B
How Investors See It: Attractive for early-stage VCs and strong for angels. Big enough to build a $50–$100M+ ARR company. Often best sweet spot for Series A/B.
Example Outcomes: Toast (restaurant POS) started in a market under $1B but layered services to grow beyond.
Evidence & References: Sequoia’s guide: $1B+ total market is a typical VC target, but $250M–$500M initial markets are common for seed.
Size: Large
TAM Range: $1B–$10B
How Investors See It: Venture scale. Multiple winners possible. Large enough to justify big raises but still not so large you’re “boiling the ocean.”
Example Outcomes: Figma (design collaboration), Canva (design tools) both began in this band.
Evidence & References: Andreessen Horowitz: most unicorns begin with TAMs in the low billions; CB Insights: median unicorn TAM at Series A is ~$4B.
Size: Extra Large
TAM Range: $10B+
How Investors See It: “Change-the-world” categories. Can attract major VC rounds very early, especially in frontier tech. Risk is that the market is too broad without a clear wedge.
Example Outcomes: OpenAI, Stripe, Airbnb.
Evidence & References: PitchBook: Top 10 VC-backed IPOs of last decade came from TAMs >$10B at founding; requires strong initial focus to win.
How to Talk About It in the Room
Don’t inflate your numbers — smart investors can smell it in seconds.
Be clear on your entry point and how you’ll grow into a bigger opportunity.
If you’re starting small, show the roadmap for expansion.
If you’re starting large, show the wedge you’ll win first.
Your goal is to be believable. I’d rather see a founder walk me through a $250M TAM they know cold, than a $50B market they clearly Googled 10 minutes before the pitch.
Tip: “Start small, think big” beats “boil the ocean.”
4. The MVP: What Are We Actually Building? (And What Will We Learn?)
A working prototype can help, but for angel rounds, it’s not required. What matters most is that you’ve got a clear game plan and a deep understanding of what you need to figure out.
This is your moment to outline what you’re building and why. More importantly, show what you still need to learn — the assumptions you’re testing, the user behavior you’re validating, and the part of the value chain you’re de-risking. You don’t need to show perfection, but you do need to show where you’re starting and where you expect it to take you.
The strongest founders don’t just describe their product — they walk investors through their thinking. They can explain what they believe to be true about the problem and solution, what they’re testing to confirm it, and how they’ll adjust based on what they learn. It’s less about showing a flawless build and more about demonstrating you have a deliberate, testable plan for turning an idea into a business. At the angel stage, that clarity of approach is often more convincing than the prototype itself.
Tip: At this stage, your MVP is less about the product and more about the plan. You’re proving you know how to get there.
This is a visual story of capturing talent — skills, location, learning — and showing how that profile is found, shared, and turned into opportunity. The images show the vision; the narrative makes it real without a finished product.
5. GTM Strategy: How Will You Make Money?
GTM is not just “we’ll launch on Product Hunt and run Google Ads.”
This is your chance to show you know who your customer is, how you’ll reach them, and how the engine grows over time. This can include enterprise sales, bottom-up adoption, channel partnerships, or community-led growth.
The best GTM slides aren’t theoretical. They’re practical and specific.
Tip: Clarity here is a signal that you know your customer better than your future competitors do.
6. Forecast: How Quickly Will This Scale?
This one’s optional at the angel/pre-seed stage, but helpful.
You're not expected to have all the answers, but rough projections over 12–24 months show you’ve thought ahead. Focus more on milestones than hockey sticks. If for example you’re raising $1M, explain what that gets you: team, product, first customers.
Investors care less about precision and more about how you think about scale.
Tip: Use this to connect “The Ask” to real, tangible outcomes.
7. Competitors: Who Else Is in the Game?
Yes, you have competitors. Pretending you don’t is a red flag.
Show you’ve done the homework. Be fair and informed. Then make the case for why your approach is better, faster, cheaper — or serving a different need entirely.
A great slide here signals confidence, not insecurity.
Tip: Bonus points if you show respect for competitors but still explain how you win.
8. The Team: Why You?
No one funds an idea. They fund the people bringing it to life.
Highlight relevant experience, domain insight, and how the team complements each other. Two is better than one — not just for skills, but for resilience. Investors want to know more than one person is carrying the weight.
If you're a solo founder, lean into your network of advisors or early collaborators. Show how you’re building strength around you.
Tip: Your experience doesn’t have to be “big exits” — just make the case that you're the right people, at the right time, solving the right problem.
9. The Ask: What Do You Need and What’s the Game Plan?
This is where many founders fall flat. Don’t just say “we’re raising $1M.” Say why.
Break down:
How much you’re raising
What it funds (team, product, GTM) and how
What milestones you’ll hit and how
It’s not just about the money, it’s about the plan. If an investor writes you a check, what happens next?
Tip: Clarity here shows you're not just pitching, you’re building.
VC FAQs: The Questions Behind the Questions
After the pitch, the questions start — and some of the most important aren’t about your numbers at all. Here’s what most VCs are testing for:
Do you believe what you’re pitching?
They may push back not because they dislike your idea, but to see if you’ll stand firm. Conviction matters as much as the concept.Do you have the passion to walk through walls?
They’re looking for grit. How do you respond to setbacks? Can you take the hits and keep moving?Do you know what you don’t know?
It’s fine not to have every answer. What matters is that you can show the gaps and have a plan to close them.Why you, and why now?
Timing can be everything. VCs want to hear why this is the right moment for this solution — and why you’re the one to lead it.What’s the biggest risk — and how will you de-risk it?
They know every early-stage venture has risk. The founders they back can call them out and explain a plan to tackle it.
Final Thought: The Story Beats the Spreadsheet
I’ve raised nearly $200M across multiple ventures. At the early stages, no one is investing in your cash flow model. They’re investing in your story.
So tell one. Frame the problem in a way that’s personal, show you’ve done the work, and be honest about what you know and what you’re still learning. Let your belief shine through, but back it up with substance.
Your deck isn’t about proving you’re perfect. It’s about proving you’re obsessed with the problem, credible in your approach, and the kind of founder who won’t quit.
That’s what gets funded.
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Thank you, Adam, for sharing your candid advice on what it takes to nail your pitch deck. Follow Adam on LinkedIn.
Level Up Community Spotlight
Community member, Lisa St. John (former Managing Director at Alibaba), hosted the first E2 - Executive Empower Growth Salon. An intimate Bay Area dinner and honest conversation between community member leaders and guest speaker Stanford GSB Professor Robert E. Siegel. The topic was how to go beyond KPIs and into long-term systems thinking. Read the highlights in Lisa’s LinkedIn post.
Keep an eye out for Lisa’s next E2 Salon in our upcoming weekly newsletter exclusive to paid subscribers (latest issue here).
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