I'm Bridget Harris, Co-founder of YouCanBook.me - Bootstrapping SaaS with a remote team. AMA!

Rajaraman, thank you for your questions - I will try!

— What does it mean when you say, culture isn’t about the vision/passion? Would love for you to unpack it.

The context here (for me at least) is a revenue-funded company, I am acutely aware of our Profit and Loss (Income Statement in the US) - and how headcount for the sake of a vanity metric can really harm it.

Hiring people is the hardest and riskiest thing to do - as you are essentially trusting people to make good decisions on your behalf (the 'principal / agent’ problem). In reality - people have people problems unrelated to your business - and giving them a ‘top down’ vision isn’t necessarily going to help motivate them.

I think the operating culture of the company - who people work with, how much autonomy do they have, can they see results, are they supported by their team and budgets, are much better ways to motivate your team than getting them to sign up to a vision.

In YCBM, a while ago, I set out our vision which was to be ‘a Tiny Company that does Big Things” which means, we want to stay small, lean and agile to enjoy the team and individuals we work with, but also to ensure we can be incredibly productive (less meetings / less management / less barriers).

We have huge ambitions for our product and the way we serve customers, but equally our day to day satisfaction comes from delivering small things repeatedly over time with great people.

— Also, how do you encourage (and enable) the rest of the team to inform/influence the org’s culture?

This is really important - and it starts with hiring the right people and avoiding the wrong people. Without going over it all, here is my 5 min guide to hiring. If I’ve done my job right - we should have hired someone who not only fits into our culture, but also knows when someone is working with us who perhaps isn’t going to be as successful in that role as we had first imagined (which still happens).

It means that we all become the keepers of our culture and the way we like to work - and what we want to do. I can see now we have some real veteran employees who’ve been with us over 5 years this is working - they know who is going to like the way we work and who is going to struggle.


Hi Shruti -that’s such a tough one! I think that, at the beginning we were so delighted and overwhelmed by huge growth and interest in our tool, we definitely just took on more than we could deal with.

Our product development was a bit all over the place, we had too many settings, tabs, features and it was driving us crazy. The free tool had complicated features we couldn’t support, the paying customers wanted other features we didn’t have time to develop because we were too busy building out capacity overall - nightmare!

We did lots of things to figure this out - but some exercises that stop out were:

  1. Identify what group of customers are most successful (and profitable for you) in using your tool, So for us, we are focussing on businesses who have large teams who need to co-ordinate meeting with their customers (like sales / customer success and so on) and other related functions like recruitment and ux research -all B2B type stuff where scheduling needs to be high quality, secure and customisable.

If you have a group of customers in mind you are building for, suddenly a huge number of things you ‘could’ do fade away as you just know they are not relevant. If you are successful at the strategcy the good news is you can come back to those other customers later in an expansion mode.

  1. When we re-jigged our pricing and our tiers, which we have sone several times and even changes our pricing model altogether, we sat down and whiteboarded all our features - just took a step back and looked at where everything currently sat, what it was doing, and how we re-jigged.

When we did this a 3rd time we knew that different pricing for different features gets increasingly complex to support legacy plans etc). So we switched to 1 simple price-per linked calendar and then you get all the features upgraded with it. It’s served us well and massively cut down on complexity.

All off this has helped, but we’re still learning - a quick plug for Bruce McCarthy as we did a product roadmap masterclass recently with him and I loved his simple walkthrough on how to prioritise and manage a roadmap as well as prune your backlog.


Thanks Murthy, I am ashamed to admit I am not a great expert on this (I should be better really). Being bootstrapped you don’t automatically get give a ‘ready made’ circle of people pushing advisors towards you, nor so you have a board structure or other ways to incentivise their support.

That said, over the years we have had 2 or 3 people we regularly look to for strategic advice, particularly when we’re tackling a big decision.

The opposite of imposter syndrome is possibly - being over-confident that you start to believe everything you do must be correct!

I also really enjoy meeting and getting to know other founders (like here of of course) as there’s nothing like shared experience to help you move things along.

So I would throw that back out to founders and ask how they have managed along the way - are paid advisors the way to go, or do you always get them through the financial channels?


Hi James - thanks for your kind words, yes I hope so too! I saw on twitter that your sister is working in the medical frontlines, I wish her and everyone else working for us right now our sincere thanks and support for what they are doing.

Competition is scary James, I won’t deny it - and actually, a bit like democrat and sausages, the least you know on how it is made the better (churchill?). Which means, if I do read blogs or follow a twitter update on a competitor I can’t help but feel that twinge of panic in my stomach that suddenly it’s all going to come tumbling down around us. So sometimes I just ignore competition and get on with my life - feels better!

However, when I do think about it, here is my basic approach

  1. Know what you need your competition for - some of it is (although you won’t believe it) actually good for you. People like to have other tools to compare with. If we didn’t have over 200 competitors then we couldn’t be one of the top 3 tools on G2 :wink:

  2. Competition is also there to remind you of the problem you are solving - there are 7 billion people on the plant - they are not all going to use the competitor’s tool just because they manage CSS or something. You can go after your customers because you know you have a good product and something they want.

  3. For YCBM, we have always been a product-led and customer-centric company. We are immersed in our customer experience of our product and therefore even if someone else decided to go with acuity or calendly or whoever, I know many others choose us because of what we do - our customer service and customisation are two differentiators I know make a big difference.

  4. I spoke once at MicroConf a few years ago about bootstrapping - I laid our all our numbers and spoke candidly (as you have seen!) about our experience.

When I got off the stage I found myself talking to two CEOs of other bootstrapped scheduling tools. I had a mini internal panic and quick review had I said anything that they could take advantage of?? And then I thought to myself, building online scheduling tool is hard - people have high expectations, and very specific needs. If one of these guys can do it better, fantastic, the world’s a better place. We had a really nice chat and I felt better for having met them and we shared our experiences.

In reality 99% of the success you achieve is because of what you do, and what you make of it - it’s not because you’ve found some secret sauce that another competitor doesn’t yet know about.

The opportunity is always in your hands - not theirs. :muscle:


Hi Krish - thanks for those questions, I really enjoyed my chat with Jane - often the ‘philosophy of free’ gets somewhat over looked as an obvious thing but as you say, there is a lot to under pin it.

Much more to say on this but I’ll give you an overview of where we are with these particular issues:

1. Customer feedback loops and product ownership

As I said in my interview with Jane, it looks us a while to realise we were actually giving ourselves a double whammy of problems giving too much away on the free tool, and at the same time having to support those features because actually they were really complicated to use and set up! We could see that people who regularly sign up free tools (of which I am one) aren’t necessarily interested in getting involved in support or the community - more they just want something to ‘work’.

So conversations with these uses wasn’t necessarily the most productive, which was one reason why we reduced access to support at the same time making the tool much more simple to use. But there are also different to people who are genuinely trialling the tool.

Separating out our signups based on these kind of intentions has been invaluable for us to target conversations with the right people - generally it’s much larger teams who are interested in our product roadmap and want to have active feedback on it. Others just want to know if we are getting a fix out for some niggling UI. Equally, we do conduct UX research across a broad range of users who we’ve invited to speak to us specifically who do not have any immediate concerns.

Having said that, we do have lots of ways to interact with everyone who uses YCBM - we have a community forum, we will set up question / survey tools which pop up after events that are particularly interesting to our UX researcher, and we will be in touch via email when appropriate. Anyone can email it, it’s just if they are on the free plan we don’t give them access to our support in our chat beacon.

The update on this is we’ve now switched to 100% free trial - so everyone has access to our support for 2 weeks, and can then track our conversations / conversions within these cohorts before they drop into the free plan.

We have a very tight feedback loop between Customer-Product-Engineering and then back again for fixes and bugs. The ownership of the product is very much led by our Head of Product - but we are small enough to make sure customers and what they tell us are at the heart of our roadmap.
To that end, out head of Customer Success runs a ‘customer spotlight’ session each month, where each member of her team contribute to a 1 hour summary of what is happening in the works of our customers that everyone in the company has to watch.

2.traditional freemium funnel

No we don’t forgoe it - we have actually just overhauled our design UI to include lots of upgrade prompts, as well as more prominent branding on YCBM pages if you are using the free version - we do over 1 million bookings a month, so it’s very important to us that all those bookings carry our branding and help promote our tool.

Here is our feature page where you can toggle between free / paid and we add prompts for popular things to do on the paid plan. But at the same time, our target market are teams and larger groups who need scheduling - who would have to pay as that involved multiple calendars (we charge per calendar links). Consequently, we don’t need to do a massive ‘Big Sell’ to the free users, as they already help us by managing their bookings on our platform,

Metrics that matter to us is activation - how soon as someone taken a booking, and activity - how many bookings does someone take. This tells us how likely it is they are going to be to carry on using our tool and also whether they are likely to want to upgrade (someone taking 1 booking a month isn’t going to feel like paying $10 for that) which makes sense.


Hi Vengat!

Yes online scheduling is full of great tools, including Calendly, but there are many others - some who serve a particular type of scheduling and so are in a specialist category. At YCBM we have a great offer for companies who need to use multiple calendars for their teams - we have positioned quite a bit of our marketing and content to focus on that (see here for an example)

The second part of your question is actually related - because we’ve been around a long time we actually have historically many thousands of active users and customers, who keep using us for their bookings- which helps push the natural viral growth loop we can rely on over and above tradition content marketing. We also have many schools and universities in America who use us which allows us to grow naturally through word of mouth.


This is a great question Logesh, and I’m sure everyone one us here has thought about it a lot and has some extra to add!

There are multiple dimensions to how we have been affected at YCBM

  1. Quite a few of our customers have been going through terrible trauma, have have their businesses cancelled overnight, and also of course could be personally affected by illness and loss. As well as making some business decisions around our tool to help them, I could also see that this was going to be a tough time for our team to help them as best we could. I wanted them to have flexibility to make offers and switch things around depending on circumstances. I wrote up a piece for our journal: which included advice not to try and expect ‘business as usual’ performance metrics and KPIs from the team, as they will be dealing with not just our own personal impact, but the impact on our customers too.

  2. Although we were already a remote team, and so people are used to working from home, I decided I wanted to be more in touch that usual with everyone. So I instituted 15 minute ‘lock down catch ups’ with everyone in the company - I’ve had one every 3 weeks or so. It means I get a chance to catch up with each of my team mates (we’re about 16 people) and find out about their individual circumstances and how they’re family is doing etc. I know that would be hard to do at scale, but I’d recommend managers and other senior people to be doing similar with their teams.

  3. We created new channels in Slack - silly stuff about music / cooking (I’m sure everyone is doing similar) and a place to post photos and updates specifically about lockdown.

  4. We just recently started a ‘Lockdown Win of the Week’ where after a nomination, a team member will get a certificate for something they’ve done to keep going which is inspiring or fun - here is our first recipient:

Maintaining team morale and culture is already a high priority for me as it’s easy to lose touch with when everyone is remote, so we were already aware of many of the pitfalls.


Hey Bridget,

Thanks for doing this AMA. We’re currently bootstrapping Progression and can see a clear path to scaling to $10,000s and even $100,000s MRR. However we can also see a less well defined path that could see us become a much bigger platform that could change the way companies and individuals think about and manage professional growth. It feels like that bigger vision would require external capital to get to and would be inherently more risky and rewarding.

Did you ever find yourself or companies you know considering a tradeoff between big vision and “bootstrapability” or is possible to combine both?

Looking forward to hear thoughts on this,


Hi Ravi, welcome to remote working! Here are my top tips :wink:

I really honestly belive that your question is (outside of financial and regulatory compliance) my number one job for the company to be successful.

More than that - it means building up a company that it’s enjoyable to work for - and there’s multiple strands to it.

  1. be realistic

First thing, some people are going to absolutely thrive working for you - others, who at face value are just as talented and skilled, simply will not. You have to forgive yourself that you may have hired someone you thought was perfect and it just doesn’t work - in which case you need to quickly move on otherwise the dissonance will bring you both down - but you can obviously learn and refine the process.

  1. Hire without hurting

I’ve linked this on another thread, but here it is again, as I wrote this to help attract those who wanted to work for us, to give them clues on how to get a job with YCBM: How to hire without hurting | YouCanBook.me.

I would say most, if not all, our recruits from the last few years mentioned they had read that piece - as well as watching some of the other things I’ve said publicly (like the Business of Software talks etc).

As well as showing genuine interest and research in the role, above all it demonstrated curiosity - a desire to find out things, which is one of the things we look for at the company. As a remote company, you can’t rely on people just discovering information floating about in the office as people are chatting. You need to find people who are purposefully and pro-actively interested in problem solving on their own initiative. How they apply to a job here at YCBM will tell us a lot about that person.

  1. be clear on team values / culture

I go on about this a lot, I interview and hire to a criteria, and I am totally open about it - we have a culture deck we use which is based on a description of ‘who we are’ and how we like to work.

I’ve learnt that if you endlessly repeat what is important to you - others become keepers of it as well, and more importantly, it answers the question ‘what is the right thing to do?’ in this situation - it’s a north star.

  1. be fair open, generous and transparent about renumeration

quick points - at YCBM we:

  1. employ everyone in their native countries - everyone is on social security / health insurance / pension protections. Employee benefits (particularly home ones) are really important to people, and they would forgo a bigger salary via a contract in return for job security and being paid via payroll. It’s a bit controversial and sometimes hard to operate it all, but I’m a believer in it and have been ever since we hired our first non UK based employee (currently we’re set up to hire in the US / Ireland / Spain

  2. Have open and transparent salary scales - we all know what everyone is paid. There’s no internal secret gaming or negotiation, there’s no gender pay stuff going on, it is what it is.

  3. pay 10% profit share to employees vested from 1.5-4 years in the company. This is deliberate as an alternative to options as we’re a wholly private company with no plans to take on VC.

At the end of the day, if you are generous and fair with your employees, they know you are playing straight and you are all on the same field. Companies who seek to make a profit by basic exploitation of their workforce should just get in the sea.

  1. Repeat, Rinse, Repeat

I’ve been running YCBM for 8 years - in that time we’ve had people come and go, mistakes and triumphs, some of the people who work for us now feel like family - they are putting their best work and their best years into our team and product. This isn’t something I take for granted and so I am concious that everything we do to allow them to do their best work is my job.


Anushree - thanks for your question!

Firstly - Bootstrapping is an art not a strategy. It’s not for everyone, some people genuinely like the cashflow and support from investors, and it works for them.

Not everyone likes to juggle the last day’s take on Stripe to manage payroll :grimacing: or weedling out last minute overdrafts from banks to keep things going. But it felt right for me and Keith my co-founder, as a way of deliberately slowing things down so we could work at exactly what we wanted to do and not take on someone else’s cash and burn it on the wrong thing.

I did a talk on it at MicroConf a few years ago, so definitely watch that, but my tips are really the same. I don’t think there’s anything particularily special about bootrapping companies, it’s actually called in another world ‘building a business’ and people have been doing it for many thousnads of years.

The difference in the last few years is the enourmous bounty on offer for being in the first wave of software tools that has attracted venture capitalists and private equity, looking for huge gains.

But that is their business model -not yours.

If you want to bootstrap, you need to know long term what your profit model looks like, and whether you can scale that with more customers without adding exponetially to costs (by having to hire more people) which would wipe out your profit.

YCBM made a loss for 5 years in a row - but we were also growing really quickly, so I knew our income loss was off set by a cash in advacnce cushion and a long term gain.

But it’s a long term thing - there are no quick wins to bootstrapping and I would recommend NOT sacrificing everything for the sake of what you want to be a 2 year flip, which turns into a 20 yearlabour of love. Your family and friends wont thank you for missing all the parties!


Hi Neil - yes definitely I did - and in fact that experience is tied into many of my answers here today about how one thing leads to a different set of decisions - about people, hiring, culture and choices.

So for example, it’s not an accident that we have built a small company, that’s profitable with a highly motivated team, which does big things but is not (yet) taking over the world.

It’s because we want to stay in control and make good, elemental decisions about the foundations of what we are building - a degree off at the start is a huge degree off 100x the scale.

So we are very product-led and customer centric. It’s people intensive, but we manage it well - YCBM has near on 18,000 customers - and many thousands more on the free plan. We have a full time customer success / support team of 5 (3 in US 2 in Europe). Our team is first class and actually won an award recently from NiceReply, Most people get their queries answered within 2-3 hours. We’ve also just been included in G2 Crowd’s top 100 software companies for 2020 which feels incredible to me. But it’s based on all of our customer feedback and the work that we’ve done.

So I do think that it’s possible to build brick by brick - assuming your product will allow you to scale (online scheduling clearly does have a huge addressable market).

I did a podcast with Alex Theuma a few years back where I talked about the way to look at such a decision and when you might want to take VC:

I think it comes down to whether your interests and theirs are truly aligned, so their money is working for you, not the other way around!
I recommend you read Founder’s Dilemma which talks about this - whether you want to be ‘rich’ (which is often correlated with VC-backed companies) or ‘king’ which is where founders keep control

and that can often be a very personal choice.

good luck - let us know how you get on!


Thank you for your question Jayashree - so much to unpack here, I’ll give it a go!

Before YCBM we had actually built another tool, whenisgood.net, which is still up and running (just about) and before that we’ve actually built a further 8 other products!

So my co-founder Keith was good at turning out products, we just hadn’t worked out how to turn them into businesses.

When we spun YCBM off from WhenisGood - the growth was palpably different - we had customer and take up immediately. i think the growth that year something like 2,000% (this was 2011) and in 2012, we knew that we had a product + customers = business.

Growth for us as always been built deep into the nature of online scheduling - one booking introduces our tool to a new person and we do around 1 million bookings a month, so we’ve been incredibly lucky that out the door we’ve had the viral loop to depend on.

But challenges with massive growth if you are bootstrapping is being able to plan ahead (ie hire) when you might not necessarily have the cash. We struggled with banks to lend us money, and eventually took out private loans to tide us over. But we broke even about 3 years ago which was a great feeling as the business model was tied to so many cost factors as well as potential for growth.

So investment in new infrastructure (we jumped ship into AWS a few years ago which took a big chunk of time and distraction)

  • investment in a new pricing model (our previous model simply wasn’t scalable)

  • investment in a new client-side app to handle all account holder settings etc

  • building our APIs + R&D

these all took massive amounts of time and energy to get right, which we did under cover of long term bootstrapped investment rather than short term considerations/

Frankly, if we had had investors in the room we would have spent half the budget on sales and marketing. But we would be dealing with the same issues (shaky infrastructure, slow UI, complex pricing) at just a bigger scale so I’m glad we did it the way we did.

on a side note - one of biggest headaches ever has been sorting our billing and subscription solution (which we have in-house) so I definitely recommend looking at all the tools available :wink:


Just want to thank everyone on here for all these great questions today- I hope I’ve answered them but do shoot me an emil bridget@youcanbook.me or on here for any follow ups.

Also - since quite a few of the the themes were about bootstrapping and product evolution, you may all be interested to know that I am due to speak with my colleague, Jonathan who is head of Product at YCBM at SaaStock Remote:

9:40 AM - 10:00 AM PDT / 5:40 PM - 6:00 PM BST

Can you take over a product from its founders?

Where we’re going to cover why we hired Jonathan, and what impact it had on our product and ability to scale and grow over the last few years.

There are tons of speakers and workshops (I’m doing another one on hiring as well we’re just finalising times)

Use my speaker discount for 20% off: HARRIS-20

Thanks Relay / Chargebee and everyone here for today :muscle: :grin: :wave:


Hey @bridget,

Thank you for taking the time out for answering all the questions in such depth and for sharing so many of your personal tips and resources! There are a ton of incredible insights in here and I’m sure it’s going to be super useful for everyone. :slight_smile:

Personally I am in awe of too many things — the sentiment and phrasing of your mission of being “a Tiny Company that does Big Things”, the fact that you have built ~10 products (wow!), the ‘Lockdown Win of the Week’ channel that you shared about, and of course, your approach to competition. :raised_hands:

So glad we could host you and get to learn from your remarkable journey. Hope to have you join us soon again! And thank you again!


Also, a big thanks to @wingman4sales, @Murthy, @jamesgill, @Anushree, @Jayashree, @raviramani, @vengat, @Logesh, and @ncameron for joining in today and asking some amazing questions.

We’ll see you now on 11th June for an AMA with Nick Franklin — Founder and CEO of Chartmogul. Hope you can join in. Stay tuned for more details! :zap:


This is brilliant thanks for taking the time to reply and for those links!


So good! Ahh thanks Bridget - awesome response. And thanks for the kind words re my sister. See you again soon, and I hope you are keeping well. Thanks for being so awesome :raised_hands:


Thanks so much for the detailed answer, very helpful! My key takeaways:

  • Less is more when it comes to product
  • One way to deliver this is through focussed segments you could still say have 10 features for each persona user type but package them such that they only see what they need to
    +Muralidharan Venkatasubramanian

Hey Bridget,

Amazing responses, here. The nuggets of learnings is gold for fellow founders. Thank you for sharing your journey and the learnings and thank you for doing the session with us.

Great to learn about how you’ve navigated the inherent challenges of the freemium model, the distinctions between free and paid users, and the importance laid on UX research for use cases across the board.



Hello Bridget,

Thanks you! Loved the behind-the-scenes take on so many of YCBM’s decisions.

Thanks for sharing such a personal window into how you think about culture.

This is admirable; wish more of us understood this:
“I think the operating culture of the company - who people work with, how much autonomy do they have, can they see results, are they supported by their team and budgets, are much better ways to motivate your team than getting them to sign up to a vision.”

Ever so often, this critical ‘how’(and the meaning) of doing things the right way gets mired in the almost obligatory, valley-driven chase of a profound ‘why’ (which, of course, is seldom as profound as it sounds and even when it is, it should never justify the everything-goes mentality we so often hear about in startups).

Thanks, again!