Software eats your calendar before it eats the world. The product takes shape, users show up, and then the real job begins. Not shipping the app. Turning it into a software business that pays rent, salaries, and the cloud bill without turning your hair gray. After a few launches that looked great on Hacker News but flat in Stripe, here are the scars and the lessons.
Lesson 1: Treat the product like a business from day one
Everything gets easier when you decide you are building a business, not a side project that somehow becomes one. That switch changes your daily choices. You start saying no to clever features and yes to boring things like billing, onboarding, and support. It is not glamorous, but it keeps money coming in and churn going down.
People do not buy software. They buy a better outcome at work. That means every screen, email, and help doc should push toward one thing customers care about. For a time tracker it is faster invoices paid on time. For a log tool it is fewer 3 a m errors. Put that outcome in your homepage copy, in your pricing page, and inside the first run flow. Ship fewer features. Ship more results.
Look around. Facebook just bought WhatsApp for a number with a lot of zeros. Distribution wins. A simple product with clear value and unfair reach beats a fancy feature list. Your job is to stack the deck with distribution that matches your customer. That leads to the next lesson.
Lesson 2: Pricing and packaging are product decisions
SaaS pricing is a lever, not a formality. It should match value and make upgrades natural. Per seat fits tools that replace a person’s time. Usage based fits data and infrastructure. Tiered makes sense when customers grow with you. Test the copy as much as the numbers. A plan named Starter that solves nothing is not a starter. A plan named Team that unlocks a team outcome will convert.
Offer a free trial when setup is light and value is fast. Use a credit card up front when onboarding is guided and serious. Free without a time limit can work when you have a growth feature baked in like shared docs or invites. Write down who your ideal customer profile is and price for them, not for everyone. If your best users are agencies, sell projects and client seats. If your best users are startups, sell monthly with fair ramps and freeze plans for dormancy.
Do reviews with customers where you ask one question. If tomorrow I doubled the price, would you stay, leave, or ask your boss. The answers tell you if you are underpricing or skating on thin ice. Track MRR from new, expansion, and churn. Expansion is where the magic lives. Land with value, expand with outcomes.
Lesson 3: Distribution beats features
In this moment of Docker buzz, CarPlay splash, and every startup wiring into Stripe, your edge is not a clever algorithm. It is reach. Pick one main channel and one backup. For a developer tool, that might be content and docs as the main channel, and GitHub integrations as the backup. For a marketing product, it might be SEO and partnerships. For internal tools, it might be outbound email with short demos.
Make friends with platforms but do not become a feature of them. The Heroku add ons page can send nice trials. So can the Shopify app store. Keep control of your list, your billing, and your story. Platforms change terms. Your list does not.
Do customer development every week. Five real conversations beat fifty guesses. Watch a new user share their screen while they try to get to their first value moment. Count the clicks. Count the minutes. Then shave both. Your growth rate is hiding in that friction.
Contrast: Bootstrapped focus and Venture scale
Both paths work. They just ask for different bets.
Bootstrapped teams trade speed for control. The customer is the boss. Cash flow sets the roadmap. You pick smaller markets and own them. Your moat is care, fast support, and a tight product that does one job better than anyone. You can take weird swings and say no to shiny news cycles. Profit is not a dirty word. It is oxygen.
Venture backed teams trade control for speed. The market is the boss. You aim for winner takes most areas with network effects, data gravity, or massive reach. You hire ahead of revenue, raise before you need it, and race for share. You do not have to make money early, but you must prove growth, retention, and strong unit economics. Burn buys time. It also shortens patience.
Pick your path on day zero and tune your choices. A bootstrapped team should not copy the sales playbook of a company with a floor full of reps. A venture backed team should not copy the minimalist funnel of a quiet indie product. Both can win. Confused strategy does not.
Practical checklist for a healthy software business
- Write a one line promise that states the result you deliver. Put it on the homepage and in the app header.
- Define your ideal customer profile. Industry, team size, job title, and the moment they feel pain.
- Map the first run path to the first value moment. Get it under five minutes and under ten clicks.
- Set one primary metric. For SaaS this is often activation to retention. Review it every week.
- Price for the outcome. Tie plans to value steps users can feel. Rename plans to match those steps.
- Ship a clean billing flow. Prorations, upgrades in place, and self serve cancel with a save path.
- Track churn with exit reasons. Fix the top two reasons before adding new features.
- Publish public docs and a changelog. Trust grows when people see momentum and clarity.
- Pick one main channel for growth. Feed it with steady content, integrations, or partnerships.
- Talk to five customers every week. Ask what they tried before you, what they pay for elsewhere, and what result would make you a must have.
- Automate support where it saves time. Keep a human in the loop for the hard threads.
- Measure payback period. Months to recover customer spend should fit your cash plan.
- Set guardrails. No custom features without a clear template to ship them for everyone later.
- Build a small moat. Data import and export, light network effects, or a workflow that becomes daily habit.
- Keep a runway view. Twelve months is comfort. Six months is focus. Three months is panic. Act before panic.
One last nudge on timing. Trends come and go. Right now messaging apps prove that simple wins when distribution multiplies it. Your product can ride a wave without being a clone. Borrow the reach idea. Keep your own taste.
Ship value, charge fairly, talk to customers, and make one thing easier every single week.