Stack
The tools I actually use to run a business — and what I tell every founder who asks.
Last updated: March 2026. This is a living document — updated periodically as tools change and new ones earn a place on the list.
I didn’t plan to start a pet business. I was surviving.
For years I had operated at the presidential level — advance work, communications, and operations across WH, DHS, HHS, and large corporations. In a world where this kind of work doesn’t always come with a steady paycheck, I had been fortunate. Contracts were reliable. Work was consistent. Then the climate shifted.
The administration in power was not exactly welcoming to those of us who had worked with certain people. Contracts dried up. Opportunities that had always been there simply weren’t anymore. That’s the reality nobody talks about in those circles. Your livelihood is tied to relationships, to who is in power, and to whether the people you’ve served are currently in favor or out of it.
I was also getting sick. Regularly, seriously sick. What appeared to be bad colds, pneumonia at various intervals. We didn’t know yet that it was foreshadowing a much more serious battle. I was fighting things most people around me didn’t know about, while still showing up and doing the work.
And then, at the start of this already difficult chapter, I lost Jessie and Keiki within 48 hours of each other. My dog and my cat. Both of them, suddenly, unexpectedly. The grief of losing an animal is real and it is profound. Losing two at once, while everything else was already on fire, that was its own kind of breaking point.
I was tired. Tired of the temp work, tired of putting on a smile for people who looked right through me, tired of waiting for something to come through. I figured there had to be a better way. So I started pet sitting.
It made sense. I loved animals. I had always worked and been around animals. I needed income. I needed a way to heal my heart. I needed something that kept me moving and kept me close to creatures who asked nothing complicated of me and wouldn’t judge me in return. I signed up for one of the big-name apps that had entered the market and I got to work.
I was good at it. Better than good. I became one of the top providers on the platform, so much so that the app reached out and asked me what my secrets were. I also had to call them and ask them to add a third digit to their pricing field. Their system only allowed you to charge up to $99 at the time. I needed to charge more.
Still, in my mind, it was a bridge. Something to carry me until the next big contract.
Then a difficult client complained, after services had already been rendered. He had asked me to book off the platform to save on fees. I agreed. What I didn’t know was that he was setting me up, planning to file a complaint and get the services for free. The platform never called me. Never asked for my side. They blacklisted me overnight. Took the money. Took the clients I’d built. Took the reviews. Took everything. And refused to hear my side of the story.
I had contact information for some of those clients. I reached out, apologized, and told them exactly what had happened. Every single one of them said the same thing: We’re staying with you. We don’t have any loyalty to this platform. We’ll go where you go.
And there I was. A side hustle that had quietly become something real. A decision in front of me. And absolutely none of the infrastructure in place to support it.
I built the website, the payment platform, the scheduling system, the email list, all of it, in a scramble. That was a good problem to have. I had clients. The rest was just stuff to figure out.
That’s the point of this article.
Your first and primary goal is to get clients. Everything else you can build as you go. I’ve watched too many smart, capable people spend six months perfecting their logo, researching tools, and crossing every T before they open their doors, and then never open them.
Get your first dollar. Then build the machine.
Here’s the machine.
Before you spend a dollar, ask yourself these questions.
Not every business needs the same foundation on day one. But these are the questions worth having answers to, even if you’re still working through some of them.
Legal and structure: Are you operating as a sole proprietor, LLC, or S-corp? Have you filed with your state? Do you have an EIN from the IRS? Do you have a registered agent? Are there state or local business licenses required in your industry? Federal requirements?
Financial: Do you have a dedicated business bank account, completely separate from your personal finances? Do you have a bookkeeper? Do you understand your tax obligations? Do you have a business credit card? Do you have a contract in place before you take on work?
Insurance: At minimum, general liability. If you’re giving advice or professional services, add professional liability, also called errors and omissions. If you’re holding client data, look at cyber liability. Don’t skip this category. I’ve seen businesses get wiped out by situations that a basic policy would have covered.
Your runway: How many months can you operate without income? Three months minimum. Seven is better. More on this below.
Your banking foundation.
Open a dedicated business checking account as soon as your LLC or business entity is set up. Mixing personal and business finances is how you create a tax nightmare, pierce your LLC protection, and make your bookkeeper want to quit. I learned this from watching other people make the mistake. Don’t be that person.
Most default to the big commercial banks. I’d push you to think differently.
If you qualify, Navy Federal Credit Union and Pentagon Federal Credit Union (PenFed) are two of my favorites. Navy Federal serves active duty military, veterans, DoD employees and contractors, and their immediate family and household members. PenFed started with a military focus but has since opened membership to everyone, no affiliation required. Both are member-owned, not-for-profit, and built to serve you rather than extract from you. Check your eligibility before you default to a bank that doesn’t have your interests at heart.
If you want a digital-first option built specifically for startups, look at Mercury or Relay. No fees, clean interfaces, and they integrate well with accounting tools.
On credit: Apply for a business credit card early, even with a small limit. You’re building a credit profile for your business separate from your personal credit. Running expenses through a dedicated card also makes bookkeeping dramatically cleaner.
I’m a fan of American Express. The points programs are genuinely valuable if you use them strategically, and the business cards come with protections and benefits that most people don’t take full advantage of. A great starting point is the Amex Blue Business Cash card — straightforward cash back on business purchases with no annual fee. If you travel regularly for your business, look seriously at the Amex Platinum. The annual fee looks steep until you actually inventory the benefits: airport lounge access, travel credits, hotel status, Global Entry and TSA PreCheck reimbursement, purchase protections, and more. For a business owner who is on the road, it often pays for itself in the first trip. The points also transfer to a wide range of airline and hotel partners, which means smart redemptions can fund travel that would otherwise come straight out of your operating budget. Know what you’re spending, know what you’re earning, and make the card work for you rather than the other way around.
The Oh Crap Account: I operate in themes of seven. Close your books within seven days of month end. And build what I call an Oh Crap Account with seven months of operating reserves. Not three. Seven. This is the money that doesn’t get touched unless everything goes sideways. It’s the difference between a bad quarter and a catastrophe. Build it before you think you need it.
Your domain.
Own your name on the internet before someone else does.
If you plan on speaking, writing, or building any kind of public profile, you need your personal domain. If you have business names, those are separate purchases. If you’re building a service-based business, consider buying the domains around your primary name as well. One strategy worth knowing: having multiple related websites that point back to your main site helps validate your presence and strengthens your search visibility. It’s a long game, but it pays off.
I use Porkbun for domain registration. Straightforward, well-priced, and it doesn’t nickel-and-dime you the way the bigger registrars do. I made the switch after Google sold their entire domain division to Squarespace. Fine, but the pricing went up and I moved on.
Go search your business name right now. If it’s available, buy it today.
While you’re at it, go claim your handle on every social media platform you can think of, even the ones you’re not planning to use yet. Instagram, TikTok, LinkedIn, Facebook, Pinterest, X, Threads, and anywhere else relevant to your industry. Your name is your brand. Reserve it before someone else does. You don’t have to be active everywhere. You just have to own the name.
Your workspace and email.
Once you have a domain, you need a professional email address. Not Gmail. Not Hotmail. Not Yahoo.
Every time I see a business card with a Gmail address on it, I think the same thing: whose company are you advertising? You are literally promoting someone else’s brand every time you hit send. If you want to be taken seriously, your email needs to end in your business name. Period.
Google Workspace handles this cleanly — email, calendar, Drive, Docs, all of it integrated and built for business. It’s what I use and recommend to almost everyone.
The exception: if you’re operating in a space where HIPAA compliance or legal data protection requirements matter, take a hard look at Microsoft 365 with Teams first. The compliance integrations can make it the smarter call. Know your industry before you commit.
Google Drive handles cloud storage and file backup within Workspace. Have a system from day one. Files scattered across your desktop is not a system.
Your website.
You need a home base. Somewhere that belongs to you, not a platform that can change its algorithm, suspend your account, or decide tomorrow that your content doesn’t fit their guidelines.
I learned that lesson operating off a platform that blacklisted me overnight. No call. No explanation. They just shut me down and took everything. Don’t build your business on someone else’s foundation.
Squarespace is one of my favorite options for getting up fast without sacrificing how it looks. Clean templates, easy to manage, no developer required.
I’m also a fan of Ghost for those who want a cleaner, more content-focused platform. If you go that route and want help with setup, I have a programmer I can refer you to.
When you’re ready to build the machine — funnels, automated email sequences, lead management, CRM — Go High Level does all of that and more. It starts at $97 a month for the Starter plan and replaces a stack of other tools. There’s a learning curve. Worth it when you’re ready. If funnels are part of your plan from day one, don’t wait. Start with the base plan and grow into it.
Whichever platform you choose, make sure your website has a privacy policy and terms of service from day one, especially if you’re collecting emails or payments. Termly and Iubenda both handle this affordably and keep you protected.
Your email list.
This is the one asset most new business owners completely overlook. It is one of the most important things you will build.
Social media followers are rented. An email list is owned. Platforms get acquired, algorithms change, accounts get suspended. Your email list goes with you no matter what. I know this from experience, not theory.
I use and recommend Substack. It’s where I publish The Jenn Files, and it gives you something rare: a publishing platform and a list you actually control, in the same place. Your subscribers are yours. That matters more than most people realize until the day a platform decides otherwise.
Start building your list before you think you need it.
Your security.
This one gets skipped. Don’t skip it.
Surfshark VPN is what I use. When you’re running a business from a coffee shop, an airport, or anywhere outside your home network, a VPN is not optional. You are protecting your clients’ data, your financial accounts, and your business. The cost is minimal. The risk of not having it is not.
1Password for password management. Once you have ten tools running you need this. It protects you and it protects your clients. Non-negotiable.
Google Authenticator for two-factor authentication codes. I use 1Password for passwords and passkeys, and Google Authenticator alongside it for an added layer of protection. Set this up early. Every account that matters should have two-factor enabled.
Your operational stack.
These are the tools that determine how money moves in and out of your business.
Invoicing and payments: Can your clients pay you easily? Square and Stripe are the two I’d look at first, depending on whether your business is primarily in-person or online. Ask yourself before you choose: do you need to add gratuity to invoices? Do you need contracts attached? HoneyBook and Dubsado both handle contracts, invoices, and client management in one place for service-based businesses and are worth a serious look.
One thing worth thinking about early: your operational tools will be shaped by your industry. Every industry has platforms built specifically for it. Generic tools work until they don’t. When I was building in the pet services space, we tested several options before landing on Time to Pet. It was built for that business model and it showed immediately. Before you default to a generic solution, research what the leading operators in your industry actually use.
Scheduling: Don’t make people email back and forth to get on your calendar. A booking link solves this in thirty seconds. Google Calendar has one built in and can be configured to collect payment as well. Calendly is another clean option.
Your phone situation: Think carefully about this one. Do you want clients to have your personal mobile number? How available do you want to be? What boundaries do you want to set from day one? If you want separation, Google Voice gives you a dedicated business number that rings your cell for free. SimpleTexting and Podium are more robust as you scale. Go High Level handles this too once you’re on that platform. There’s no universal right answer, but make a conscious choice rather than defaulting into one you’ll regret.
Contracts and e-signatures: Get a contract in place before you do a single dollar of work. Adobe Acrobat is my first choice. HelloSign and DocuSign are both solid options. If you don’t have a contract attorney, use a vetted template from a lawyer who specializes in your industry. A handshake is not a contract. I’ve seen what happens when people skip this step. It isn’t pretty.
Automation: Once you have a few tools running, you’ll want them talking to each other. This is where automation platforms come in. Think of Make (my preference over Zapier) as the connectors between your software. When someone fills out a form on your website, automation can trigger an email response, add them to your CRM, notify you via text, and create a task in your project management tool, all without you touching anything. It sounds complex. It isn’t once you see it in action. Start simple, one or two automations that handle your most repetitive tasks, and build from there.
Your books.
Get this set up before you need it. Not after your first tax season. Before.
Wave is where I’d start. Built for small business, clean, and handles the basics without overwhelming you. I’ve used it. It does the job.
When you’re ready to level up, look at Digits. It’s the AI-native accounting platform built for modern business — automated bookkeeping, real-time insights, invoicing, bill pay, all of it. It starts at $100 a month and it’s more equipped than anything else in the space right now. More money than Wave, but a genuinely different category of capability.
The broader landscape has changed significantly. Xero, FreshBooks, and a growing number of AI-native tools are all worth looking at depending on your volume and complexity. QuickBooks is still out there but it’s not the only answer and it’s not always the right one.
Remember the seven rule: close your books within seven days of month end, every month. Not quarterly. Not when you get around to it. Seven days. It’s the only way to actually know where your business stands.
What matters more than any software is having someone in your corner who knows how to use it. I work with a bookkeeper I trust completely. If you’d like a referral introduction, reach out to me directly.
Do not wait on this. Get a good bookkeeper and a good accountant in place before you think you need them. That relationship is worth more than any software on this list.
Your AI stack.
We live in a different world now. A lean, focused business owner with the right AI tools can move faster and operate smarter than teams twice the size did five years ago. What used to require a full staff is now enabling solopreneurs to build and scale real businesses. The playing field has shifted. A single person with the right tools can now compete with operations ten times their size. That’s not a prediction. It’s already happening.
Claude is my primary AI, where I do my thinking, my writing, and my strategy work. ChatGPT has its place and I maintain a paid membership there as well. If you’re in the Google Workspace ecosystem, Gemini is already baked in. These aren’t gimmicks. They’re part of how modern businesses operate. Get familiar with at least one of them from day one.
Blotato is what I use for social media content repurposing and scheduling. You create once and distribute everywhere. For a business owner without a team, this is the difference between a consistent presence and radio silence.
I also want to specifically mention Sabrina Ramonov. She’s a Forbes 30 Under 30 honoree who founded and exited an AI company acquired by Pegasystems, and she now runs Blotato and is on a mission to teach ten million people how to use AI, for free. She has built one of the most practical, accessible libraries of AI education available for small business owners and founders. She also recently launched Women Build AI, a community for women building with artificial intelligence. Start with her free resources at sabrina.dev. If you are serious about learning how AI can work inside your business, she is one of the best people to learn from.
Don’t leave money on the table.
Two tools that require almost no effort and pay you back on purchases you’re already making.
Rakuten gives you cash back at thousands of retailers — stores you’re already buying from. Sign up, shop through the portal, get paid. It’s one of the simplest ways to recover money you’d otherwise leave behind. This is my referral link — we both benefit when you sign up.
Beyond cash back, think about how you’re earning on every dollar your business spends. The right credit card rewards program, the right cash back tools, the right loyalty programs — none of them require extra work. They just require paying attention.
The things nobody puts on the list.
Your working hours, and who knows them. You set the culture of your business from day one, including the culture around your own time. A service business will consume every hour you allow it to. Decide what your boundaries are, then hold them. This is harder than it sounds and more important than most people realize until they’re burned out and wondering what happened.
Your Oh Crap Account. Seven months of operating reserves in an account you do not touch unless you absolutely have to. Not three months. Seven. Build it early. Protect it fiercely. The businesses that survive hard seasons are the ones that planned for them. I’ve seen businesses that looked strong from the outside collapse because they had nothing in reserve when one bad month turned into two.
One more thing.
I built a seven-figure business from a 13-inch laptop, a mobile phone, online tools, and relentless focus and grit. I did it while fighting for my health. I did it while grieving. I did it when the contracts dried up and the options narrowed and the easy path disappeared.
The infrastructure matters. This list is real and worth building.
But none of it means anything without clients.
Get your first one. Then your second. Let the business tell you what it needs. Then build the machine to support it.
The businesses that make it aren’t the ones with the most tools. They’re the ones that moved.
Quick reference: everything in this article.
Banking and credit
Navy Federal Credit Union — military and family eligibility
PenFed Credit Union — open to everyone
Mercury — digital-first business banking
Relay — digital-first business banking
American Express Blue Business Cash — cash back, no annual fee (referral link)
American Express Platinum — travel benefits, lounge access, TSA PreCheck reimbursement
Domain and identity
Porkbun — domain registration
Workspace and email
Google Workspace — email, calendar, Drive, Docs (referral link)
Microsoft 365 with Teams — for HIPAA and legal compliance environments
Website
Squarespace — fast, clean, no developer required
Ghost — content-focused platform
Go High Level — funnels, CRM, email, automation, starts at $97/month (referral link)
Termly — privacy policy and terms of service
Iubenda — privacy policy and terms of service
Email list
Substack — publishing platform and owned email list
Security
Surfshark VPN — VPN protection (referral link)
1Password — password management
Google Authenticator — two-factor authentication
Payments and invoicing
Square — in-person and online payments
Stripe — online payments
HoneyBook — contracts, invoices, client management
Dubsado — contracts, invoices, client management
Time to Pet — pet services industry platform
Scheduling
Google Calendar — booking links, payment collection
Calendly — scheduling
Phone and texting
Google Voice — free business number
SimpleTexting — business texting
Podium — messaging and reviews
Contracts and e-signatures
Adobe Acrobat — e-signatures and contracts
HelloSign — e-signatures
DocuSign — e-signatures
Automation
Books and accounting
Wave — small business accounting (referral link)
Digits — AI-native accounting, starts at $100/month
Xero — accounting software
FreshBooks — accounting software
AI and social
Claude — primary AI for writing, strategy, and thinking
ChatGPT — AI assistant
Gemini — AI integrated with Google Workspace
Blotato — social media repurposing and scheduling
Sabrina Ramonov free AI resources — AI education for business owners
Women Build AI — community for women building with AI
Cash back and rewards
Rakuten — cash back on everyday purchases (referral link)
American Express Blue Business Cash — cash back on business purchases (referral link)
Ready to build this out with someone who’s done it? That’s exactly what I do. Let’s talk.
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