Podcast Episode: Tech Stack Truths: Simplifying Software Decisions with Vicki Pollack

Let me start with a confession: I’ve been in tech stack hell for the last two years, and it’s been one of the most frustrating, expensive, and educational experiences of my entire entrepreneurial journey.

If you’re reading this while paralyzed by tech decisions, overwhelmed by platform options, or currently juggling five different software subscriptions that barely talk to each other – this post is for you.

I’m about to take you on the messy, expensive journey of my tech stack evolution. Not because I’m proud of it, but because I wish someone had been brutally honest with me about this part of building a digital business.

The Beginning: When “Free” Actually Made Sense

When I started selling digital products in July 2023, I made one of the smartest decisions of my entire journey: I chose SystemIO.

Why? It’s completely free until you hit 2,000 email subscribers.

Do you know how long it takes the average person to get 2,000 email subscribers? Statistically speaking, a really long time. So why not use a free tool to get there?

SystemIO became my all-in-one solution:

• Sales funnels ✓
• Email marketing ✓
• Product delivery ✓
• Course hosting ✓

Here’s the kicker: I made my first $500,000 using SystemIO.

Let me repeat that because it’s important – I built a half-million-dollar business using free software that most “gurus” would tell you isn’t sophisticated enough.

The First Crack: When Limitations Become Roadblocks

Once I hit 2,000 subscribers, I started paying $97/month for SystemIO. And that’s when I really started noticing its limitations:

• Random automation glitches
• Clunky connection between purchases and product delivery
• Not aesthetically pleasing (if pretty emails matter to you)
• Very elementary drag-and-drop functionality

But here’s what I learned: most tech is awesome to a point. That point comes when you hit the software’s limitations, and then you have to decide: can I live with this, or do I need to pivot?

The Shiny Object Syndrome Begins

This is where my story gets expensive and embarrassing.

Instead of asking “What do I actually need right now?”, I started asking “What might I need in the future?”

Mistake #1: I added StanStore ($99/month) while keeping SystemIO ($97/month)

Why? Because I wanted to sell individual digital products, and StanStore made that simple. So now I’m paying $196/month for two platforms doing similar things.

Mistake #2: I discovered Funnel Freedom

Funnel Freedom is a “white label Go High Level product” (fancy way of saying someone repackaged existing software). What attracted me? 365 pre-written emails with affiliate links already embedded.

Sounds brilliant, right?

Wrong. Those emails weren’t FTC compliant, promoted products I didn’t believe in, and made me feel icky about what was going out with my name on it. I lasted maybe 6 weeks.

The Platform Hopping Madness

Here’s where things got really out of hand. I was now juggling:

• ThriveCart for checkouts
• Searchy.io (now Membership.io) for course hosting
• FlowDesk for email marketing
• StanStore for product links
• Showit for my website
• Zapier to connect everything together

Can you see the problem? I was duct-taping my entire business together on the backend.

When someone bought something, it had to trigger 4-5 different platforms to work correctly. When one Zapier connection broke (and they break constantly), my entire system fell apart.

I was spending more time fixing broken automations than actually running my business.

The Kajabi Migration: Finally Some Peace

In October 2024, I hired someone to move everything into Kajabi. Best decision I made all year.

Suddenly, everything lived in one place:

• Website ✓
• Email marketing ✓
• Course hosting ✓
• Checkout pages ✓
• Automations that actually worked ✓

For the first time in months, I felt confident sending people to my website because I knew everything would work correctly.

Kajabi costs $219/month, but it replaced about $400/month in other software.

The Plot Twist: When Paid Ads Changed Everything

Just when I thought I’d found tech stack peace, I started running paid advertisements. And paid ads exposed a new problem: Kajabi’s upsell capabilities are limited.

When you’re spending thousands on ads, your checkout experience needs to be optimized for conversions. Kajabi’s upsell pages can’t be customized without coding knowledge (which I don’t have).

So now I’m back to using SamCart ($179/month) for checkouts while keeping Kajabi for everything else.

Yes, I’m zapping platforms together again. Yes, it’s giving me agita. But when you’re spending serious money on ads, conversion optimization becomes critical.

The Brutal Truth About Tech Stack Decisions

After 2 years and probably $15,000+ in software experiments, here’s what I’ve learned:

There Is No Perfect Platform

Every single piece of software has limitations. SystemIO is clunky but free. Kajabi is beautiful but expensive. StanStore is beginner-friendly but limited.

Stop looking for perfect – it doesn’t exist.

Your Needs Will Change

What works at $0 revenue won’t work at $100K revenue. What works with 100 email subscribers won’t work with 10,000.

Plan for where you are now, not where you think you’ll be.

Integration Headaches Are Real

The more platforms you use, the more things can break. Every additional software adds complexity and potential failure points.

Simplicity beats sophistication every time.

The Decision Paralysis Is the Real Enemy

I spent 2 weeks comparing SamCart vs ThriveCart. Two weeks! That’s time I could have spent creating content, serving customers, or literally anything else productive.

A fast decision beats a perfect decision.

My Honest Platform Reviews

Since I’ve used literally everything, here are my brutal honest takes:

For Complete Beginners: StanStore

• Pros: Incredibly intuitive, great support, handles everything you need starting out
• Cons: $99/month from day one, limited customization as you grow
• Best for: Anyone who’s not tech-savvy and wants to start selling immediately

For Tech-Savvy Beginners: SystemIO

• Pros: Free until 2,000 subscribers, full functionality, good learning platform
• Cons: Clunky interface, frequent glitches, not aesthetically pleasing
• Best for: People who don’t mind figuring things out and want to minimize costs

For Scaling Businesses: Kajabi

• Pros: Professional, reliable, all-in-one solution, excellent customer experience
• Cons: Expensive ($219/month), limited checkout customization
• Best for: Businesses ready to invest in professional tools and user experience

For Checkout Optimization: SamCart

• Pros: Highest conversion rates, incredible customization, slide checkouts
• Cons: Expensive ($179/month), only does checkouts well
• Best for: Businesses running paid ads or selling high-ticket items

The Questions You Should Actually Ask

Instead of “What’s the best platform?”, ask yourself:

1. What do I prioritize right now? Cost? Ease of use? Customization? Professional appearance?
   
2. What’s my actual budget? Not what you hope to afford, but what you can afford today.
   
3. How tech-savvy am I honestly? Don’t overestimate your abilities or patience for learning new software.
   
4. What’s my revenue goal for the next 6 months? Choose tools that serve that goal, not your 5-year vision.
   

My Recommendations Based on Where You Are

If you’re making $0-$10K/month:

Use StanStore if you want simplicity, SystemIO if you want to save money and don’t mind a learning curve.

If you’re making $10K-$50K/month:

Consider upgrading to Kajabi for the professional experience and reliability.

If you’re making $50K+/month:

Invest in optimization tools like SamCart for checkouts, especially if running paid ads.

If you’re running paid advertisements:

Your checkout experience is critical. Invest in conversion-optimized tools even if they’re more expensive.

How to Escape Tech Stack Hell

If you’re currently drowning in platform decisions, here’s how to get out:

1. List your actual needs (not wants, needs)
2. Set a decision deadline (I give myself max 3 days for any tech decision)
3. Pick based on your current situation, not future possibilities
4. Commit for at least 6 months before reconsidering
5. Track what’s working so you can make informed decisions later

The Bottom Line

I’ve been through tech stack hell so you don’t have to. The truth is, the platform matters way less than your ability to execute consistently within whatever platform you choose.

Stop overthinking your tech stack and start building your business.

The most successful entrepreneurs I know aren’t the ones with the most sophisticated tech – they’re the ones who picked something that worked and focused on serving their customers instead of optimizing their software.

Your business won’t fail because you chose the “wrong” platform. It’ll fail because you spent so much time choosing platforms that you forgot to actually build something people want to buy.

Pick a platform, commit to it, and get back to the work that actually moves your business forward.

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