''' I’ve seen it all. After sitting on the investor side of the table for 200+ deals and founding two companies that got acquired, I can tell you that most fundraising advice is garbage. Especially when it comes to your timeline.
Want to know the real reason investors are passing on your startup? It’s not your pitch deck, your traction, or even your team. It’s your timeline. You’re thinking about it all wrong.
The Timeline Most Founders Pitch (and Why It’s Wrong)
I’ve reviewed over 500 pitches in the last few years. A shocking 90% of them have a slide that looks something like this:
- Month 1-2: Finish product V1
- Month 3-4: Onboard first 1,000 users
- Month 5-6: Raise Series A
- Month 7-8: Scale to 10,000 users
- Month 9-12: Reach $1M ARR
Looks reasonable, right? Wrong. This timeline tells me one thing: you have no idea how long things actually take. You’re optimistic. And in the startup world, optimism that isn’t grounded in reality is a liability.
When I see a timeline like this, I know the founder hasn’t accounted for the brutal realities of the fundraising process. They think it’s a neat, two-month affair. It’s not. It’s a grueling, all-consuming marathon that will distract you from your actual business.
My "Oh Sh*t" Moment with Fundraising Timelines
With my first company, MovieLaLa, we had a timeline just like that. We were young, ambitious, and naive. We thought we could just waltz into investor meetings and walk out with a check.
We were so wrong.
Our initial timeline had us raising our seed round in 6 weeks. It took us 5 months. 5 months of hearing "no," getting ghosted, and constantly tweaking our pitch. All while trying to build a product and keep our early users happy. It was a nightmare. That experience taught me a lesson I’ll never forget: fundraising always takes longer than you think.
The 1% Approach to Fundraising Timelines
So, how do the top 1% of founders do it differently? They treat fundraising as a continuous process, not a discrete event. They build relationships with investors long before they need the money.
Here’s what their timeline looks like:
- 6-12 Months Before Fundraising:
- Identify a target list of 50-100 investors.
- Get warm intros to the top 20.
- Start sending them monthly updates. Not asking for money, just sharing progress.
- 3-6 Months Before Fundraising:
- Start taking informal meetings. Coffee chats, not formal pitches.
- Get feedback on your business and your deck.
- Build a genuine connection.
- The "Official" Fundraise (2-3 Months):
- This is when you flip the switch. You tell your warm leads that you’re officially raising.
- Because you’ve already built the relationship, the process is much faster. They already know you, your business, and your progress.
- You’re not starting from zero. You’re starting from the 50-yard line.
This is how you run a fundraising process that doesn’t kill your company. You play the long game.
A Note on Series A and Revenue-Based Financing
This approach is especially critical when you’re raising a Series A. The stakes are higher, the diligence is more intense, and the investors are more sophisticated. You can’t just show up with a good story. You need to show a pattern of execution over time.
I’m also a big fan of exploring revenue-based financing, especially for SaaS companies with predictable revenue. It’s a great way to get non-dilutive capital to fuel your growth without getting on the venture capital hamster wheel too early. We used a form of it at RemoteTeam to help us scale before our acquisition by Gusto. It gave us breathing room and allowed us to grow on our own terms.
Stop Pitching, Start Building Relationships
If there’s one thing you take away from this article, it’s this: stop thinking about your fundraising timeline in terms of months and start thinking about it in terms of relationships. The best founders are always fundraising, even when they don’t need the money.
Now go update your timeline. And for God’s sake, stop being so optimistic. '''
Frequently Asked Questions
What's the most common pushback you get on this?
People often push back by citing exceptions or edge cases. And they're usually right that exceptions exist. But building a strategy around exceptions rather than patterns is a losing game for most founders.
How can I apply this thinking to my own situation?
Start by identifying the core principle behind the opinion, not the specific example. Then ask yourself: does this principle apply to my context? If yes, test it in a small, low-risk way before going all in.
What experience informs this perspective?
This perspective comes from over a decade of building companies in Silicon Valley, two successful exits (RemoteTeam to Gusto, MovieLaLa to Gfycat), and investing in 200+ startups including Anthropic, OpenAI, and Scale AI. I write about what I've lived.
Do all experts agree with this view?
No, and that's fine. The best ideas in business are often contrarian. I share my perspective based on my experience and data, but I encourage you to seek out opposing viewpoints and form your own conclusions.