When you’re running a business, there’s this constant question in the back of your mind: Should I invest in this, or should I find a cheaper option?
I remember in my early days of entrepreneurship, I wanted everything to look polished and feel professional, but I didn’t have thousands of dollars to throw at every tool and upgrade. I made expensive mistakes, not by spending too much, but by waiting too long to invest in the right things.
Here’s one that still makes me cringe: I was doing paper contracts and checks in the mail for years. I had this massive filing cabinet (that I’m still too afraid to get rid of) and spent hours every week going to the bank, filing paperwork, and sorting through client documents. The expensive mistake wasn’t buying something fancy I didn’t need. It was waiting too long to invest in a client management system like HoneyBook that could handle contracts, payments, and my entire client pipeline in one place.
The cost of not investing was eating up my time and energy, and I was confident I could earn back the monthly fee within days. That’s when I learned my most important business lesson: sometimes the biggest risk is waiting too long to make smart investments.
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My Business Investment Decision Matrix
Being an entrepreneur means making what feels like a million decisions every day. Research shows the average adult makes over 35,000 decisions daily, and entrepreneurs face even more. No wonder decision fatigue is real.
That’s where my decision matrix comes in. It’s the filter I use to quickly separate smart splurges from strategic saves:
Splurge when it: directly impacts revenue, builds customer trust, or saves significant time and stress.
Save when it: supports behind-the-scenes operations and an affordable option gets you 80-90% of the functionality.
The Four Questions That Guide Every Business Purchase
- Will this help me make money in the next 3-6 months?
- Will this save me significant time or reduce stress?
- Will my customers notice the difference?
- Is there an affordable option that works almost as well?
When I’m torn between two similar tools, I don’t just think about my current business—I consider where I want to be in two years. The cost of switching platforms later often outweighs paying slightly more upfront for something that can grow with you.
And here’s my reality check for investment guilt: I look at what it’s costing me NOT to make the investment. How much time and energy am I wasting without this solution? Could I earn back this investment amount with that reclaimed time? Usually, the answer is yes.
SAVE: Email Marketing with Flodesk
Email marketing is where the sales happen, where you nurture relationships, and where you show up for your audience without competing with social media algorithms. But here’s the truth most platforms don’t advertise: they charge you more as your list grows.
Back when I was building my first list, I remember dreading that moment when I’d cross into a new “tier” and suddenly my monthly bill would double, just because more people wanted to hear from me. It felt like being penalized for doing good work.
Enter Flodesk. A flat monthly rate, no matter how many subscribers you have. Stunning templates that look like you hired a designer. Easy drag-and-drop features that don’t require coding or hours of setup. The first time I sent a campaign through Flodesk, I couldn’t believe how elevated it looked without paying for custom design.
Now, every time my list grows, it’s a celebration instead of a budget headache. According to industry data, most small business owners spend $20-50 monthly on email marketing, and Flodesk keeps you at the lower end while delivering premium results.
Why it’s a save: Accessible pricing + incredibly smart features + beautiful templates = professional results without the growing pains.
RELATED: Flodesk vs. Mailchimp: Pros, Cons, and Which One Wins?
SAVE: Social Scheduling with Tailwind
If there’s one lesson I’ve learned about marketing, it’s this: consistency matters more than perfection. Showing up regularly keeps you top-of-mind, but manually posting every day is exhausting.
When I found Tailwind, it felt like such relief. Instead of trying to keep up with multiple platforms, I could batch content in one sitting and schedule it out for weeks. Tailwind was built with Pinterest in mind, but it also works beautifully for social media.
One of my favorite features is Tailwind Create, which helps me turn one idea into multiple, on-brand pin designs in minutes. That means more content out in the world without me spending hours in Canva. I’ve tried bigger, more expensive scheduling tools, but honestly? They were overwhelming and overbuilt.
Tailwind is simple, affordable, and designed for entrepreneurs who need their time back without the complexity of enterprise-level platforms.
Why it’s a save: Keeps you consistent without enterprise-level complexity or cost.
RELATED: The Comprehensive Guide to Using Pinterest for ANY Business Type
SAVE: Stock Photos with Elevae Visuals
There was a time when I thought I had to shoot every single image myself to keep my brand consistent. But as life got busier (cue motherhood, running a business, and always launching courses), I realized I couldn’t always be behind the camera.
The challenge with most stock photos? They look generic and don’t feel like your brand. And visuals really need to feel like you, because they go everywhere: freebies, social posts, Pinterest, webinar slides, landing pages, thank you pages, and emails.
That’s why I love Elevae Visuals. Their collections are cohesive, elevated, and designed with entrepreneurs in mind. I use them for blog headers, email graphics, social content, and sales pages. The photos look like they came from a custom brand shoot but cost a fraction of the price.
Plus, they add fresh images monthly and even offer a curation service. It means I can keep my brand visuals polished even when I don’t have capacity for a new shoot, and that peace of mind is priceless.
Why it’s a save: Professional, cohesive imagery at membership pricing instead of custom shoot costs.
SPLURGE: Client Management with HoneyBook
This is the investment I wish I’d made years sooner. I was doing paper contracts and checks in the mail, with a filing cabinet I’m still too afraid to get rid of. I spent hours every week going to the bank, filing paperwork, and sorting through client documents.
The expensive mistake wasn’t buying something fancy I didn’t need, it was waiting too long to invest in a solution. HoneyBook handles contracts, payments, questionnaires, and your entire client pipeline in one seamless system.
Instead of paper everything, clients can sign contracts and pay invoices instantly. The time savings alone paid for itself within weeks, not to mention the professional experience it creates for your clients. When you’re spending hours on administrative tasks that could be automated, you’re actually losing money by not investing.
HoneyBook streamlined my entire client experience from first inquiry to final payment, and I wish I hadn’t waited so long to make the switch.
Why it’s a splurge: Your time is worth more than the monthly fee, and clients notice the smooth experience.
SPLURGE: Tonic Site Shop Templates
Your website is often someone’s first impression of your business, and we all know how quickly those form online. Early on, I tried to DIY my site to save money. Let’s just say, it looked like it. I was embarrassed to send people there, and I know it cost me clients.
When I invested in a Tonic template, everything shifted. Not only did it look incredible, but it was also strategically designed to convert visitors into clients and buyers. Tonic Site Shop’s templates are hand-crafted by my brilliant friend and web designer, Jen Olmstead, who knows exactly what kind of designs captivate your dream customers.
Here’s my contrarian take: skip the fully custom website. Templates are tried and true, easier to customize, and you’re not trapped waiting for a developer every time you need a simple change. I could customize a Tonic design to fit my brand, knowing it was built on a foundation of strategy and beauty.
Custom websites often trap you in developer dependency, while quality templates give you professional results with the freedom to make changes yourself.
Why it’s a splurge: A boring, outdated website costs you real sales every day.
Take a look at my 5 favorite Tonic Site Shop Templates! I wonder which one you’ll like most?
RELATED: Are TONIC Site Shop Website and Social Media Templates Really Worth the Price?
SPLURGE: Course & Membership Hosting with Kajabi
If you sell courses or memberships, your platform isn’t just a tool, it’s your storefront. It’s where people pay, learn, and interact with your content. The experience needs to be seamless, or you’ll lose sales.
Ever since I created my very first course a decade ago, I’ve been using Kajabi. It’s helped me host over 100,000 students, and they’re always adding smart, innovative features with course creators in mind.
Kajabi increased my conversions because the checkout process is smooth, the delivery experience is professional, and the automations save me hours each week. Honestly, one extra sale per launch often covers the entire monthly cost. When students have a frustrating experience accessing their content, they ask for refunds.
The platform you choose directly impacts your revenue, student satisfaction, and your time investment in customer support and technical issues.
Why it’s a splurge: Seamless systems, higher conversions, and better student experience justify the investment.
RELATED: Kajabi vs. Thinkific vs. Teachable (2025): Best Platform for Online Course Creators
SAVE: Lead-Generating Quizzes with Interact
Quizzes are one of my favorite ways to grow an email list. They’re interactive, fun, and convert at higher rates than most freebies. In fact, one of our quizzes brought in over 100,000 leads alone. But in the beginning, I thought building one meant hiring a developer or learning complicated tech.
That’s why I love Interact. It’s plug-and-play, with templates that make creating a quiz simple. I’ve built “What’s your style?” quizzes in less than an hour and connected them directly to my email platform for automatic segmentation.
Instead of dropping thousands on custom coding, Interact lets you test and learn quickly. And once you see how well they work, you’ll be hooked. The ROI on a well-designed quiz is incredible when you consider the lifetime value of each email subscriber.
Most freebies convert at 1-3%, but quizzes regularly convert at 15-25% or higher, making the investment worthwhile for serious list growth.
Why it’s a save: High-converting list growth tool that pays for itself quickly with plans starting at just $27 a month.
RELATED: How to Boost Your Flodesk Email Campaigns (and Sales!) with Interact Quizzes
SPLURGE: Education & Mentorship
This is where I never hesitate to invest. Whether it’s a mastermind, course, or coaching, investing in mentorship has always given me the highest return on investment.
Think about it: you can pay once to learn something new and then reap the rewards indefinitely. Paying for mentorship means you skip the headaches and pitfalls of guessing your way through business growth alone.
There have been seasons where I felt stuck, unsure of my next move. Every time I invested in guidance, I walked away with clarity, confidence, and shortcuts that saved me years of trial and error. The right mentor can help you avoid costly mistakes and identify opportunities you wouldn’t see on your own.
My litmus test: Will this investment unlock revenue, save substantial time, or reduce risk within the next 90-180 days? If the answer is yes, it’s worth it.
Why it’s a splurge: Knowledge compounds, it keeps paying you back indefinitely.
Shop My Business Stack
Want the quick version? Here’s a list of the tools I recommend:
- Email → Flodesk. Flat-rate, beautiful emails
- Scheduling → Tailwind. Pinterest + social planning
- Stock Photos → Elevae Visuals. Modern, elevated libraries
- Contracts → HoneyBook. Track contracts and invoices with ease
- Website Design → Tonic Site Shop. Beautiful, designed to convert
- Courses/Memberships → Kajabi. All-in-one platform
- Quizzes → Interact. List growth + segmentation
- Education → The JK Business Hub. My courses, masterclasses, and freebies in one place
What Tools Should I Invest in First?
For businesses making $0-$50k annually: Start with the essentials—email marketing (Flodesk), consistent visibility (Tailwind), and professional visuals (Elevae Visuals). Most successful small businesses spend $100-300 monthly on core tools.
For businesses making $50k-$100k annually: Add client management (HoneyBook), professional website templates (Tonic), and targeted list growth tools (Interact). You can afford to invest in tools that save significant time.
For businesses making $100k+ annually: Invest in advanced platforms (Kajabi), ongoing education, and systems that support scale. At this level, the cost of not having the right tools often exceeds their price.
Business Investment FAQs
Q: What should I invest in as an entrepreneur first?
A: Start with tools that directly impact revenue: email marketing, consistent content scheduling, and professional visuals. Once you’re making steady sales, invest in client management and education to scale faster.
Q: How do I know if a business expense is worth it?
A: Ask yourself: Will this help me make money, save significant time, or improve my customer’s experience within the next 3-6 months? If it doesn’t do at least one of those three things, it’s probably not worth it yet.
Q: What’s the biggest mistake entrepreneurs make with money?
A: Splurging on things that look impressive (fancy equipment, custom everything) before investing in tools that actually drive sales and visibility. Always prioritize spending on what grows your reach and leads to conversions.
Q: Should I buy custom or use templates for my business?
A: Templates, hands down. Custom websites and courses often trap you in developer dependency. Quality templates are tried and true, easier to customize, and let you make changes without waiting for someone else.
Q: How much should I budget for business tools monthly?
A: Most successful small businesses spend 5-10% of their monthly revenue on tools and software. Start with $100-200 monthly for essentials, then scale your tool budget as your revenue grows.
Confident Money Moves in Your Business
Building a business isn’t about spending the least amount of money, it’s about spending wisely. The trick is knowing where your dollars will create real momentum and where affordable options serve you just as well.
Splurge on areas that impact how people experience your brand and decide to buy from you: your website, client management, course platforms, and your own growth through education. Save on behind-the-scenes tools like email platforms, schedulers, and stock photos where smart, budget-friendly options get you most of the way there.
Remember: the most expensive mistake isn’t spending too much, it’s waiting too long to invest in solutions that could be saving you time and making you money right now.
The goal isn’t perfection, it’s progress. When you make money decisions through this lens, you’re not just buying tools, you’re building a business that’s both sustainable and scalable.
