By Chris M Walker, founder and CEO of Legiit
Most startup advice comes from people who’ve never built anything.
I’ve built multiple 7-figure companies. Bootstrapped. Scaled. Sold.
Here’s what actually matters when it comes to funding your startup.
Pitching Without VC Connections (It’s Not About Who You Know)
Everyone thinks you need connections to get funding.
Wrong.
I’ve raised money. I’ve also built companies that didn’t need it.
Here’s what investors actually want to see:
✅ A real problem you’re solving
✅ Proof people will pay for your solution
✅ Numbers that make sense
✅ A team that can execute
That’s it.
Your network doesn’t matter if your fundamentals are weak.
Your fundamentals don’t need a network if they’re strong.
Most founders spend more time networking than building. Big mistake.
Build first. Network second.
Show traction. Show revenue. Show growth.
The money will find you.
Bootstrapping vs. Raising Capital (The Real Trade-off)
I’ve done both.
Bootstrapping forces discipline. Every dollar matters. Every decision counts.
Raising capital gives you speed. But it costs control.
Here’s how I think about it:
Bootstrap when:
- You can generate revenue quickly
- Your market isn’t winner-take-all
- You want to keep control
- You’re not in a rush
Raise capital when:
- You need speed to market
- Competition is fierce
- You’re in a capital intensive business
- The market opportunity is massive
With Legiit, I bootstrapped because I could.
Revenue from day one. Profit from month two.
No investors to answer to. No board meetings. No dilution.
That freedom is worth more than money to me.
But that’s not every business.
Know which one you’re building.
Competing with Giants (How Legiit Beat Billion-Dollar Platforms)
Legiit competes with Upwork and Fiverr.
They have billions. We had a hustle.
Here’s how we won:
1. We picked our lane
They try to be everything to everyone.
We focused on quality services for business owners who care about results.
Niche wins.
2. We listened
Big platforms don’t have time for individual feedback.
We read every message. Fixed every problem. Built what users asked for.
Speed beats size.
3. We built community
They have users. We have fans.
People don’t just use Legiit. They recommend it.
Community is the best moat you can build.
The lesson?
You don’t need to be bigger. You need to be better.
Equity Dilution (What They Don’t Tell You)
Every funding round costs you ownership.
Most founders don’t think about this until it’s too late.
Here’s what matters:
Only raise what you need to hit your next milestone.
Don’t raise $2M if $500K gets you there.
Understand the terms beyond valuation.
Liquidation preferences can kill your upside.
Keep control as long as possible.
Lose control, lose your company.
I started with 100% of my companies.
I still own the majority of everything I’ve built.
That’s not luck. That’s planning.
Valuing Your Startup (The Operator’s View)
Forget the fancy models.
Here’s what actually determines value:
- Revenue
- Growth rate
- Profit margins
- Customer acquisition cost
- Customer lifetime value
- Market size
Everything else is noise.
Your startup is worth what someone will pay for it.
And what someone will pay depends on how much money it makes.
Focus on the fundamentals.
Revenue solves most valuation problems.
2025 Trends That Actually Matter
Every year, someone publishes a list of trends.
Most are garbage.
Here are the ones that will actually impact your business:
AI automation – Not just ChatGPT. Real workflow automation.
Niche markets – Mass market is dead. Serve 1,000 people perfectly.
Creator economy – People want to own their income.
Remote tools – The office is never coming back.
Sustainable business – Not just green washing. Real impact.
Don’t chase trends.
Find the trend that fits your business.
Then execute better than everyone else.
The Bottom Line
Building a startup is hard.
Funding makes it harder, not easier.
Before you raise money, ask yourself:
Do I need this? Or do I just want it?
Money doesn’t solve problems. It amplifies them.
If your business doesn’t work without funding, it won’t work with it.
Build something people want.
Charge what it’s worth.
Keep what you earn.
Everything else is details.
Want to build a business that actually works? Stop looking for shortcuts. Start building value.
That’s how you win.
About Author:
Chris M Walker is a serial entrepreneur and industry leader with deep expertise in SEO, entrepreneurship, AI, SaaS, content marketing, ecommerce, analytics and digital strategy. He is the founder and CEO of Legiit, a fast growing freelance marketplace empowering professionals to scale their services globally. Chris also leads SuperstarSEO Agency, SuperstarSEO Academy, Audiit.io and Legiit Leads and manages a thriving community of over 100k members in the SuperstarSEO Facebook Group
Known for building multiple successful ventures without outside capital Chris offers practical insight into startup growth bootstrapping gig economy leadership and online monetization. His hands on experience and strategic mindset make him a trusted voice among digital founders and early stage entrepreneurs
Chris is a member of the Forbes Tech Council and has been recognized across major platforms for his impact in tech and digital entrepreneurship
