I’m an entrepreneurial growth leader that has sold more than $25M of software, services, and physical products. Over the last decade, I’ve raised money, started and sold a company, built and led teams, and led revenue growth for companies in several industries.

Might be obvious, but before you raise VC, really ask yourself: Do I need VC?

Most founders assume they need venture capital. It's the default path. But it's also the most demanding path: in time, in equity, and in expectations.

VC makes sense if you're targeting a massive market and need millions in capital to scale fast. But if you're building something profitable in a niche? You probably don't need it.

The alternative: bootstrap or do a small angel round and grow with profits.

A lot of companies are not VC investable because they're just not targeting a big enough market. And that's fine. It doesn't mean the company isn't valuable. It just means VC isn't the right fit.

Before you spend six months fundraising, ask what the capital is actually for. Is it for software? AI can do most of that now. Is it for growth? Early enterprise sales is just sweat equity: pounding the pavement, working your network.

What do you actually need capital for?

Jon Caldwell

Founder @ 3Victor | 1x Exit | Fractional growth operator for tech & services founders | $25M+ in sales of software, hardware, and services

We found that agencies closed at the same speed as brands. But at 10 times the price.

I was working with a SaaS company selling to physical product brands, CPG companies that sold in retail and online. They also had a few agency customers who worked with those brands.

We pulled the historical data into a spreadsheet. Columns for industry, company size, buyer title. Rows for each customer. Added contract value, sales cycle length, time to payment.

The agencies stood out immediately. Same number of touchpoints. Same time to close. Ten times the revenue.

Why? Each agency dealt with 5 to 20 brand customers. Closing one agency was the equivalent of getting multiple brands on board with no added complexity in the sales cycle.

We rebuilt the entire outbound strategy around agencies. Messaging. Targeting. Even the packaging.

Sometimes the answer is already in your data. You just haven't organized it to see the pattern.

One question 38x'd our pricing model: "What stops you from using this?"

We were selling software for $30 to $40 per month. Cheap. Easy to sign up for. But usage was low and churn was high.

In customer interviews, we stopped talking about the product and started asking about their experience. What had they tried before? What got in the way?

The answer kept coming back: implementation. They wanted the outcomes but didn't have time to figure out the setup.

So we bundled done-for-you services with the software. Setup. Configuration. Ongoing management. The package went from $40/month to $1,500-2,500/month.

Close rate more than doubled.

Turns out people didn't want cheaper software. They wanted the problem solved. The higher price signaled we'd actually solve it.

If you're stuck on pricing, try asking customers what stops them from getting value. The friction point is usually the opportunity.

I doubled my posting frequency. Impressions tripled.

I'm testing this with my own account right now, and I saw the same thing with a client.

When you post twice a day instead of once, you don't just get twice the reach. You get three times the impressions. Engagements doubled.

The relationship is non-linear.

LinkedIn wants to promote people who are posting frequently and consistently. If you stick with it for three to six months, they'll give you access to a wider and wider audience.

One of my clients saw website traffic increase four to five times over a few months. Most of that was driven by LinkedIn.

The algorithm is rewarding volume more than most people realize.

The terrain dictates the strategy.

Your terrain is your market. Who you're selling to. What you're selling. The channels you're going to use to reach them.

There's a huge difference between spinning up 10,000 SEO pages for organic traffic and building an enterprise sales team with $300K-a-year sellers.

Your economics are different. Your timeline is different. Your capital needs are different.

A lot of founders copy strategies from companies in completely different markets. They see what worked for someone else and assume it'll work for them.

But the terrain is different. The strategy has to be different too.

Before you build your playbook, understand your market. TAM. Deal size. Sales cycle. Channel economics.

Then let the terrain dictate what you do next.

Give away free product. But make it conditional.

Early stage, you need social proof. You need case studies. You need testimonials on your website that say this actually works.

Here's how to get them fast:

Find potential customers. Offer them free product. But make it conditional.

"I'll give you this for free, but I need two things. First, feedback: tell me what you liked, what you didn't, how we can make it better. Second, if you like it, I need a testimonial. Your name, your company, a quote I can put on my site."

That's it. You're not asking for money. You're asking for honest feedback and permission to share their experience.

When I went to retail with my first company, I had eight months of five-star Amazon reviews. When I talked to distributors, it was "check out our reviews, we're crushing it." Way more compelling than "trust me."

If you need social proof, try giving product away with conditions attached.

Hiring more BDRs isn’t the solution. 
It’s a shortcut that rarely works anymore.

Fifteen reps cost at least 75 grand a month, plus management overhead. 
Most will underperform in six months. 
You end up cycle after cycle of hiring, training, replacing.

The real shift? 
It’s about the tools, not headcount. 

I worked with a client whose SDR was wasting 15 hours a week on manual research: copying from LinkedIn, hunting down tech stacks, updating spreadsheets. 

We threw in some automation. 
Built an AI agent that handles all that in hours. 
It identifies decision-makers, verifies tech, ranks prospects. 
Accuracy? 90 percent (equal to a human).

Two years ago, I paid a dollar for a personalized first line. Now, AI generates them for half a penny.

That’s the game changer. 

One skilled person plus the right tools can outperform a team burning through cash.

Before you ask for more bodies, ask yourself: 
Is this a people problem or a tools problem?

taplio

Jon Caldwell's Linkedin Analytics

Jon Caldwell

Performance ScoreJon Caldwell's LinkedIn Performance

Jon Caldwell's Best Posts (last 30 days)

Ready to grow your LinkedIn presence?

taplio

.css-6ytdur{background-image:linear-gradient(284deg, rgba(39, 43, 72, 1) 0%, rgba(33, 47, 183, 1) 100%);color:transparent;-webkit-background-clip:text;background-clip:text;}Jon Caldwell's Linkedin Analytics

Jon Caldwell

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Jon Caldwell's LinkedIn Performance

Jon Caldwell's Best Posts .css-1emoo84{font-size:var(--chakra-fontSizes-md);font-weight:400;color:var(--chakra-colors-gray-600);}(last 30 days)

Ready to grow your LinkedIn presence?

Jon Caldwell's Linkedin Analytics

Performance ScoreJon Caldwell's LinkedIn Performance

Jon Caldwell's Best Posts (last 30 days)