At Business of Software, we often hear from founders:

“We’ve built something that people genuinely use and value. But we have no idea how to price it.”

It’s a common and challenging problem. Pricing decisions are rarely straightforward; they come loaded with uncertainty, emotion, and long-term consequences.

This is the part no one really prepares you for.

The Emotional Weight of Pricing

You might assume pricing is a matter of strategy and spreadsheets. But talk to any founder, and they’ll tell you it’s more personal than that.

Pricing touches everything: your product’s perceived value, your brand, your customer base, and your business model. Too high, and you may scare off the right users. Too low, and you risk undervaluing the very thing you’ve worked hard to build.

It’s not just about getting the number “right.” It’s about understanding what your product truly means to your customers, and how to reflect that in the way you charge.

A Trusted Resource from the BoS Community

Years ago, Neil Davidson (co-founder of Redgate Software and founder of Business of Software Conference) faced the same pricing challenges. When he couldn’t find a clear guide to pricing for software companies, he wrote one.

The guide, Don’t Just Roll the Dice, has since become one of the most downloaded and shared resources in the Business of Software (BoS) community. At just 60 pages, it’s clear, practical, and written by someone who gets what you’re going through.

Even if it has been written years ago, Don’t Just Roll the Dice is still relevant and useful not because it gives one magic answer, but because it speaks to founders in a way that makes sense.

A Few Takeaways from the Guide

1. Value > Cost

Your pricing should reflect the value your customers receive, not your internal costs. “Cost-plus” pricing often misses the mark.

2. Segment Your Customers

Not everyone has the same needs or willingness to pay. Thoughtful segmentation opens the door to more sustainable pricing models.

3. Pricing is Perception

Cognitive biases (like anchoring and price-quality assumptions) play a major role in how prices are perceived. Pricing is as much psychology as it is math.

4. It’s Never Final

Pricing isn’t something you set once and forget. The most successful companies treat it as a process: testing, adjusting, and learning over time.

5. Getting it Wrong Has Consequences

Pricing errors compound. The wrong decision early on can shape customer expectations and limit future flexibility.

Get Your Free Copy

60 pages. 1 hour read. Years of pricing confidence.

If you’re figuring out your pricing right now (or helping someone who is), this is worth your time. And if you find the guide valuable, share it with your team.

And if you’ve already read it, we’d love to hear: What was the biggest mindset shift it gave you? Let’s keep the conversation going.

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I’m very sad to report that Mikey Trafton has died, unexpectedly and far too young.

Mikey was an extraordinary human. He was introduced to us by Jason Cohen at WP Engine who told me I should have him speak. Jason said Mikey was a brilliant story-teller with an exceptional ability to communicate and explain though definitely not one of those folk who are, ‘on the speaking circuit’. That was true, but Mikey was so much more than that. He was a delightful person who always left you happier and smarter after you spoke with him.

He attended 8 Business of Software Conferences and spoke at four of them. He was not only a brilliant speaker, people that spent time with him would often mention what a kind and generous person he was. He even made someone ‘like’ hiring.

I, and the BoS community, have lost a great friend.

Mikey’s BoS Talks have become classics and perhaps no surprise that every single talk was about people and teams.

How to Build a World Class Culture in 3 Easy Steps

A talk that started with Mikey describing how his entire team walked out on him which made him realize how important culture was. This talk helped techies to understand the framework underlying company culture and what you can do about it.

Recruiting a Bad-ass Team

As it sounds. How can you decide the kind of people that you want to work with and then make sure that they make the choice to work with you.

How To Manage Your Badass Team

Again, self-explantory but filled with super-practical advice and ideas about how to lead well.

Finding Your Super Powers

My personal favorite as it made me realise I had spent a significant part of my life worrying that I’m terrible at x or y and need to get better, when I really probably should have been thinking about how I can do more of the stuff I love and am great at, then find a way to work with people who love the stuff I am bad at.

Our deepest condolences to his parents, Dot & Jack, the love of his life, Charlotte, their two children Owen and Meredith, his family and all those who were proud to know him and consider him a friend. 

Mikey, you will be sorely missed. Know that you have made a difference.

Cambridge delivered. And so did you.

Last week, founders, product leaders, and software builders from across the globe gathered in the historic halls of Churchill College for two days of insight-packed talks, honest conversations, and the kind of community you don’t find just anywhere.

BoS Europe 2025 wasn’t just a conference. It was a chance to step out of the day-to-day and spend time with people who actually get it: The highs, the lows and everything in between when building great software businesses.

Before everything…Missed BoS Europe?

We’ll send you the talks as soon as they’re available.

Day 1 Highlights

We kicked things off with Ryan Singer, who dove into the importance of framing and how to guide teams through hard conversations with clarity, not chaos.

Melissa Appel followed with a guide for founders on understanding what product teams really need to thrive, straight from the trenches of hands-on experience.

Then Greg Baugues took us into the world of AI with practical (and magical), real-time demos that showed just how powerful (and accessible) today’s tools really are.

Over lunch, Birds of a Feather discussions sparked conversations about growth, leadership and the future of SaaS.

Robin Landy explored how to find and price features customers will actually pay more for: An essential skill in today’s product landscape.

In the afternoon, Elizabeth Lawley took us on a surprising journey through her experiment building an AI girlfriend, sharing lessons on connection, rapid MVPs and the human side of tech.

We ended the day with dinner, drinks, and a fascinating talk from Professor Alex van Someren on national security, innovation, and the crucial role SMEs play in tech progress.

Day 2 Highlights

Tuesday we started with Bob Moesta, who, (as always) helped us to see a different approach to hiring, discussing JTBD framework.

Sara Gordon delivered a masterclass on emotion-driven positioning using the Seven Deadly Sins.

David Pereira gave a no-fluff framework for product discovery that puts outcomes over output.

In the afternoon, we’ve had Mark Stephens, Chika Emebo & Nadir Shah showing us their journey on building IDR Solutions, and how to scale trust and customer relationships at a global level.

Also, Diego de Jódar made us rethink post-sale metrics and customer activation.

After break, we’ve had the chance to see 2 amazing Lightning Talks: Steve McLeod and Gareth Marlow. Two short, sharp insights into how teams really make product decisions and why imposter syndrome doesn’t have to stop you from leading.

We’ve ended the last day with an conversation with Bridget Harris, who delivered a raw, real reflection on building and selling her SaaS business after 15 years of bootstrapping.

The Magic of BoS

Every BoS conference delivers top-tier content, but the real magic is in the people.

The generosity and the shared purpose of this community is what makes it special. You could feel it in the breakout sessions, during dinner conversations and over pints in the afternoon after the talks.

A massive thank you to our speakers, our amazing supporters, Quiet Light and IG CloudOps, and of course, every single attendee who came ready to share, learn and connect.

Be the first to access the talks from BoS Europe

You may not be in the room, but that doesn’t mean you have to miss out. Want the talks as soon as they’re available? We’ll send them straight to your inbox.

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Lightning talks are back at Business of Software Conference. They are fast, focused and packed with insights – sharp perspectives from experts, leaving you with actionable takeaways in just 7.5 minutes.

At BoS Europe 2025, we’re featuring two standout applications that discusses some of the biggest challenges in leadership and product development. Meet Steve McLeod and Gareth Marlow, two experts with practical wisdom to share.

At BoS, trust and meaningful connections are at the core of what we do. We have never and will never sell attendee, speaker or community contact details. Your information is private, and we keep it that way. If you ever receive a message claiming otherwise, it’s simply not true.

Twice a year, the Business of Software Conference brings together some of the sharpest minds in software, product, and entrepreneurship. But this isn’t just another conference, it’s a place where your assumptions get challenged, your ideas get stretched, and you walk away seeing things in a whole new light.

Next in-person conference: BoS Europe 2025 on 31 March-1 April in Cambridge, UK

This year’s BoS Europe presents a group of thinkers, doers, and industry rebels who’ll make you question everything from user activation to AI, hiring, and pricing strategies. Here are the discussions that will shake up your thinking and give you the tools to build and grow a better business..

At Business of Software (BoS), we believe conferences are about building relationships that lead to significant change, not just for insightful conversations. Over the years we have received many accounts of guests who met at BoS and went on to collaborate and create amazing things.

Mark Stephens and Chika Emebo from IDR Solutions, loyal participants in our community, joined us on our first podcast episode, along with Dr. Chris Bell and Jamie Woolf from Creativity Partners, to share about their partnership.

Remember Lighting Talks? By popular demand… We’re bringing them back for BoS Conference Europe (March 31-April 1). What are Lighting Talks? Why should you consider applying for a Lightning Talk? What makes a great Lightning Talk? How do you apply and how do we select the speakers?

What are Lightning Talks?

• Lighting Talks are a difficult, fun, and entertaining opportunity for our attendees to share something they care about with other attendees.
• Attendee Lighting Talks follow a fixed format. 15 slides, without animations, that advance automatically every 30 seconds to deliver the nugget of an idea that get people to think.

Black Friday Sucks!

Ah, Black Friday. That one special day of the year when retailers desperately offload their leftovers at “bargain” prices you didn’t even know existed (or needed). It’s become the tradition – convincing you to buy stuff you don’t want with money you don’t have while your critical thinking is still in turkey coma.

We could talk all day about how this retail circus has gone global, invading inboxes and spamming your sanity with ALL CAPS DEALS!!! But let’s cut to the chase: Black Friday is bonkers, and we think it sucks.

So we’re doing something about it.

BoS Bytes: 3 Things to Make You Smarter

There’s a ton of terrible content out there. Three golden nuggets I guarantee are worth your time.

Matt Lerner’s Turing X SYSTM London Growth Summit. 6th November, London, UK.

Speakers:

• April Dunford – Positioning expert and author of Obviously Awesome
• Sean Ellis – The OG Growth Hacker, inventor of the North Star Metric, High Tempo Testing and the “Sean Ellis Test” of product/market fit.
• Joanna Wiebe – Copyhackers.com, world’s expert on direct-response copywriting
• Alex Depledge, MBE – Serial entrepreneur who founded and sold Hassle.com and currently runs Resi
• Hannah Parvaz – Founder, Aperture, 4X head of growth, award-winning mobile growth expert
• Andrew Davies – Serial entrepreneur, growth expert and current CMO @ Paddle
• Matt Lerner – SYSTM founder, bestselling author, ex-PayPal, ex 500 Startups VC

We’re exploring the heart of business growth—the messy middle. It’s that unpredictable, often chaotic phase between the excitement of starting up and the satisfaction of exiting a business. This is where the real challenges and opportunities lie. It’s not just about launching or planning your exit; it’s about navigating the complexities of scaling, optimizing, and sustaining your business in an ever-evolving landscape.

BoS Conference’s main focus is addressing this crucial stage, providing you with the tools and insights needed to thrive amidst uncertainty and turn challenges into opportunities. We’re not just discussing theory; we’re providing a roadmap through the messy middle of business growth.

Cue in Mark Littlewood’s superpower…

BoS Bytes: 3 Things to Make You Smarter

There’s a ton of terrible content out there. Three golden nuggets I guarantee are worth your time.

Can You Bootstrap a $ Billion Business?

Of course you can. It isn’t common but it can be done and there are some well known ones – Mailchimp for example. Here’s an example of one that you probably haven’t heard of – PDQ.com

Shawn Anderson, co-founder and (ex)CEO of PDQ.com has been to 21 Business of Software Conferences, first time in 2008. I guess he’s learned some good things along the way.

Shawn will be joining us to speak at BoS Conference USA, 23-35 September, Raleigh, NC and will share the story of his 20 year journey from consulting company, through utterly unfundable product business, to growth, acquisition, and his retirement from a $billion business. We’re sharing a little of the story here, part preview, part inspiration, part reminder that it takes work to build a company but there is no single right way.

Who is Shawn Anderson and What is PDQ.com?

Shawn explains who he is and what that company you have never heard of does.

Founding PDQ and the Difficult Transition from Consulting to Product Company

Every software consultancy wants to be a product business. It’s rare to make it. Shawn shares the origins of the company and the moment they decided to go all in on product.

No Venture Everything Gained

VCs are renowned unicorn hunters so looking back, funding should be easy. Shawn explains why VCs refused to invest and the implications of having to build the company without external funding. Turns out, there is a significant upside…

What Will You be Talking About At BoS Conference USA 2024, 23-25 September?

Shawn shares a short preview of some of the insights he wants to share at this year’s conference.

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