Shane Wilson's Blog

For over 100 years, going to Hollywood and making it on the big screen has been the dream of would-be actors, writers, and directors often mythologized in the kind of self-referential, self-congratulation the entertainment business is famous for.  Northern California earned its place in the global dreamscape more recently, but for the engineers, hackers, and technologists the “Bay Area” is a symbol for finding silicon riches and global product/market fit.

I landed in San Francisco in June 2025, fresh out of business school and living outside of my tight NJ-NY-CT circle for the first time in the 30ish years of my life.  Perhaps I’m jaded, or just too proud to admit that I’m a dreamer, but I didn’t really lean-in to this magical journey story on my way out here.  I’ve set my sights on becoming a startup investor, which to overstretch the Hollywood analogy means I’m looking more for positions in the mail room at CAA in hopes of working myself up to the top tiers of the business one day.  Far less romantic, far less creative, but perhaps equally as soul crushing.

To build my network and make my patagonia vest dreams come true I’ve spent as much time as I can meeting founders at events.  If you’ve never trolled the meetup.coms or the lumas of the world, here’s the scene:

75 people wearing nametags mill around a downtown open floor office space picking at a spread of lukewarm La Croixs and 50 CostCo Pizzas.  Most are men aged between 22 and 42 dressed in raggedy t-shirts, ill-fitting jeans, and beat up tennis shoes.  Conversations are awkward, forced, and oftentimes the most gregarious in the crowd are selling something: outsourced engineering firms, recruiters, occasionally the enterprising founder pushing some MVP+1 piece of hardware.  People fulfill the customary chit chat expectations before they flash LinkedIn QR codes then move on to the next pod of talkers.  The room gradually fills until it’s time to find a seat and listen to the prepared remarks: a panel, a fireside chat, a few demos. After a few ‘pick me’ Q&As the event ends with a whimper.  People rip off their name stickers on the way out the door.  They trudge back to studio apartments and low-dollar hostels to reboot their terminals and get back to building.  

These are not glamorous events (though sometimes, the spread is noticeably better- looking at you GitHub) but they are undoubtedly part of 2025’s tech dream story.  These are the counterparts to LA’s casting calls and auditions.  Everyone here knows their big break probably won’t happen tonight, but maybe the right intro can lead to something else which unlocks a breakthrough that puts you on the front page of TechCrunch or across the table from Sequoia.  This is the grunt work that silicon dreams are made of. 

Working on your pitch, your trailer, and your screenplay

I’m not an engineer. I’m not a co-founder.  So I have an outsider-looking-in perspective on these events.  I like to shake a few hands, do some chit chatting, but really my place is to sit back, take notes, synthesize observations and occasionally identify a founder or company that I want to help.

That help is almost always focused on better storytelling and strategic thinking.

Early stage startups are their founders’ babies.  They want to talk about every cute little feature they’ve built and how much time they’ve put into this.  They usually do an ok job of sharing why they’re the right person to build their product or deliver their service. They may even be so bold as to say what they aim to raise and at what valuation. Here’s what they usually miss:

• The problem that they’re solving is never communicated in the first 3 sentences.
• I don’t hear enough ‘unique insight’ on the market or users.
• They rarely define their market or explain competitive context.
• I’ve yet to hear a clearly articulated GTM strategy either on stage or in small settings.
• I want to know what the world looks like after their product reaches maturity.

Fixing these issues does not require a PhD.  It doesn’t mean you need to go out and hire an external branding and marketing firm.  It’s a challenge for founders to step out of their shoes and see their work from an outsider’s perspective.  To see themselves in the seats of the cinema, watching their film with a bucket of popcorn and fresh eyes (keep stretching that metaphor). 

This Summer, I’ve stepped on set with about half a dozen founders who I’ve met at events that I think are either individually compelling or building a product that could matter.  Here are a few things I’ve seen, suggested, and corrected:

Do your homework

Every VC and Accelerator is flooding the content market with podcast content these days.  Didn’t get into YC? Well you can still listen to what Michael Seibel looked for across hundreds of thousands of applications- here’s a start. Taking the time to explain (sit down and write it out) the problem, your product, traction, competition, market, and business model will improve your clarity of thought, help your team set priorities, and help you tell better stories. 

For the love of God, practice!

Do not, do not, do not get on stage without practicing.  It is rude to your audience and it reflects poorly on you.  If you spend the first 3 minutes fumbling with cables and loading screens, your audience is gone.  Good pitches have a beginning, a middle, and an end.  They package takeaways for listeners to remember.  They have a point.  This is especially problematic among technical founders.  If you wouldn’t ship an update with a major bug, you shouldn’t ship a presentation without any practice.  Doing either conveys to the audience that you’re not a serious professional. 

AI slop makes you look sloppy

“It’s not ______ —- it’s ____”.  Every time I see an emdash or a string of ChatGPT’s stilted ‘180 sentences’ in publicly facing content I want to scream.  We know you’re going to use AI to write your copy and that’s ok.  Take the time to prompt the model well including sample ideas, rough drafts, and tangible examples.  Don’t offboard your story to a robot.  If you do, you’ll sound cheap and unoriginal like everyone else.  

Storytelling by channel

Everything you want to say about your product does not belong on the front page of your website.  Your website is an opportunity to introduce your product, explain what problems it solves, tell us who you solve that problem for with a few examples, and most importantly- capture interest.  This is a lot to get across in the ~12 seconds users will give you on a first visit.  Your company origin story is a blog post.  The research behind your project should be a whitepaper.  Your TAM/SAM/SOM belongs in an investor deck.  Being tactical about what stories you’re telling and where will help your users quickly understand your product.  What doesn’t belong on the website front page may be the basis of your blog or resources section, a great first exercise in developing a brand and external marketing muscle.  

Are you going on stage for a 5 minute ‘speed pitch’?  Curate your messaging for this short form setting.  Then go further and make a 90 second version. Then a 60 second version.  There’s a reason movies make trailers- capture attention and convince an audience you’re worth more of their time in the future.  Don’t try to shoehorn everything into a short session and DO NOT roll up to the microphone unprepared.  

Don’t put an investor section on your website

I recognize funding may be your primary goal, but getting funded should not be the primary purpose of your website.  Your goal is to capture users who have very short attention spans.  If an investor visits your site, she is going to know what she’s looking for.  She wants to know about the Problem, Product, Traction, Demonstration, Team etc.  She will take the 5-10 minutes to find this information on your site even if it takes a few clicks.  Maybe she’ll read your “For Investors” page, but she certainly won’t stop her inquiry there.

What you should do is make sure that the key questions Investors seek to answer (again, see YC Content) are accessible but not primary.  Skip the ‘for investors’ section entirely.  If you think a good investor is going to read this section and say “Oh this is everything I wanted to know, thanks for gathering.  I’ll now leave your site and request a pitch meeting!” you’re crazy.

Help with Heuristics

You may believe your product is truly FOAK.  Chances are, it’s not.  And that’s ok.  Even if you are inventing something entirely new, it’s very difficult to understand what you’re talking about without some context. Take your marketing tag line a step deeper and help your user understand how to think about your company and why they should care.  Some examples:

“We’re completely rewriting the book on the Artificial Intelligence” < “We’re an ML Ops company that’s fixing what [BIG ML OPS COMPANY EVERYONE KNOWS] is getting wrong”

“We’re a gamechanger for anyone developing code” < “In early pilots, our product has saved ML Engineers an average of __hrs per day and have reduced compute costs by __%”

“We’re disrupting the entire social media influencer landscape” < “One thing marketing agencies get wrong is _____”

People want to believe in new products, ideas, and services.  They don’t want to use their imaginations.  Think about systematically introducing your product in a way that reduces cognitive load.  

Think about the full journey

If you’re a founder, you’re on a 10 year journey if you prove successful.  It’s really hard to see 10 years into the future, but trying to is worthwhile.  Where is this thing going if everything goes right?  Is it the next facebook? Or is this is a great lifestyle business that will make you wealthy and allow you to be your own boss?  Imaging this, then doing some backward induction is the perfect exercise of crafting an early stage strategy.  Will it change? Inevitably.  But practicing backward induction regularly means you will be able to quickly adapt and operationalize new strategies when faced with different challenges.  It will give early stage investors and pilot customers confidence they’re signing on for a journey with a qualified captain.  

Remember the questions people asked

Feedback is golden, but it’s rare someone you first meet will feel comfortable sharing openly and honestly.  When it does happen, founders often feel bruised that their product isn’t as loved as they feel it should be.  In most instances, the feedback you receive comes in the form of questions.  Are you getting the same type of questions again and again? This is a great hint to go back, re-work the story and better answer this theme.

A demo is worth 1,000 words

Are you cramming words onto your website? Or deck? If your product is demo-able, make a quick 10-45 second breeze-through demo that shows users how to use the product.  Sending over an email? Make a GIF.  Loom is a great way to put these together.