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

Hi all - I am Bridget - I’ve been running YCBM since 2012, we’ve built up a profitable, bootstrapped multi-$m company.

We serve thousands of customers and users - generating over 1,000,000 bookings a month for them.

I’d love to engage with this community on topics such as remote ops / bootstrapping / creating profit / hiring / managing teams / culture / designing and building products.

I’ve spoken before at Business of Software / SaaStock / Microconf, and love meeting founders and sharing highs and lows of building a company and product.

Please go ahead and ask whatever’s on your mind and we’ll see where the discussion takes us :slight_smile: :+1:

The AMA is scheduled for next Thursday: 28th May at 5 PM BST


Note: This AMA is closed for new questions, but you can check out the existing conversations below.

In this AMA, we had Bridget Harris — co-founder and CEO of YouCanBook.me — share her thoughtful insights on being self-funded, doing freemium right, thinking about competition, and more. Dive in!

AMA Index (Bridget’s brain pickings) :brain:

(founding insights, opinions, and observations; deftly examined and articulated)

Hiring’s “principal/agent” problem
What has helped in better defining YCBM’s roadmap; less is more
On bringing in advisors for bootstrapped companies; “The opposite of imposter syndrome is possibly - being over-confident that you start to believe everything you do must be correct!”
“Know what you need your competition for - some of it is (although you won’t believe it) actually good for you.”
How drawing a strong line between free and paid usage provided invaluable for YCBM
Brief note on YCBM’s continuously expanding viral loops
Sustaining team morale during chaotic times
The real work of allowing people to do their best work; “I really honestly belive that your question is (outside of financial and regulatory compliance) my number one job for the company to be successful.”
“Bootstrapping is an art, not a strategy.”
How Bridget has deliberated over decisions that inform building a lean, profitable team; “a degree off at the start is a huge degree off 100x the scale”
Some challenges of breakout growth as experienced at a bootstrapped business

Further reading/listening/pondering from the interwebz :open_book:/:headphones:

(Other insightful excerpts drawn from blog posts, interviews, and conversations)

On hiring, culture, and leadership:

“So how do you get the best people to work for you? …it’s roughly around culture, processes, product and leadership. And anybody can say one of those things will make the critical difference. …I think that your company is made up of people who spend money on building and selling products and services. I think the material point here is people who spend money – it’s not about vision or an exciting solution or passion. It comes down to the success of your business, to people who spend money.”
Source: Hiring The Best Talent | Bridget Harris, YouCanBook.me | BoS USA 2017

On bootstrapping successfully, having advisors, and understanding risk:

  • “We do have some longstanding advisors who have seen us through over the years, many a time when me and Keith have wondered what on earth we’re doing. When you find yourself trying to explain how you’ve decided to solve a problem to somebody else who you trust and admire and you realize that you sound a bit ridiculous, you think oh, I better figure that out. We’re always, always learning. We’ve hired lots of people who have come with them lots of experience of working with other companies. We’re very open that we need to learn as a company and as a team about how to grow and not take anything for granted. The fact that we don’t have the external board of investors doesn’t mean we’re not open to external ideas.”

  • “…the biggest thing I’ve learned about running a business is that you really have to understand risk. There’s a lot of rhetoric about business visionaries and leaders and “what’s the magic dust to do with Richard Branson” or why do people do this in the first place. My own take on it is that you need to have a very good idea of what risk you are taking, how you define that risk and what happens if your gamble doesn’t pay off, and you have to face the consequences of disaster, for example. Having that ability to not exactly know where you’re going and trust an outcome that you’re hoping is going to work based on your own hard work, it’s a good toolkit.”
    Source: Bridget Harris on bootstrapping your startup

On making freemium work for you:

  • “Build a really good free version. Build a free product that does just what it says on the tin. Nobody is ever going to complain about it. And you don’t have to negotiate with anybody about what it is. And then, as a second product essentially, build a paid-for version of the free version. Don’t try to build one product that you throw lots of features into and hope that somebody would pay at the top end for one slice of it.”

  • “Now, when it’s free, you end up with a lot of people who don’t make any choice at all. They just think it’s free. They sign up. They get going. And, they kind of, essentially, if you’ve left them a forest of features to have them find their way through, then they get exhausted trying to figure out what all of this does. So you kind of force them to figure out all these complicated features which they would have figured out had they paid you for that. Bizarrely, people are more willing to give you their time if they’ve paid you for it.”
    Source: UI Breakfast Podcast. Episode 64: Making Freemium Work with Bridget Harris

Stay in touch: :sunny:

You can follow Bridget to stay updated with her discoveries and insights:

  1. Bridget on Twitter
  2. Bridget on LinkedIn

Hey Bridget,

Thanks for doing this session!

Heard your insightful BoS talk on how you’ve thought about the significance of culture from the very beginning. This unusual frame of thinking, in particular, caught my attention:

“I think that your company is made up of people who spend money on building and selling products and services. I think the material point here is people who spend money – it’s not about vision or an exciting solution or passion. It comes down to the success of your business, to people who spend money.”

— What does it mean when you say, culture isn’t about the vision/passion? Would love for you to unpack it.
— Also, how do you encourage (and enable) the rest of the team to inform/influence the org’s culture?



As you evolved through different iterations of your product, how did you get better at figuring out what to keep and what to throw and what to modify instead?
How has this helped you in getting better in defining product roadmap for YCBM?


Thanks for this session.

How you went about building trusted network of advisors. What kind of reward structure you set for them.


Hi Bridget!

Thanks so much for offering to do an AMA on here, and I hope you are keeping well!

I absolutely love your no-nonsense approach – I always remember speaking with you at SaaStock – you cut through so much hot air that can sometimes spew from the world of SaaS.

YouCanBookMe – as with most of SaaS – is in a very competitive market. Does that keep you up at night? Do you spend much time thinking about competitors? Have you made any significant decisions because of competition that you either regret or are glad about?

Thanks in advance, and I hope we can meet up again once we’re back on something closer to normality.


Hi Bridget,

Thanks so much for doing this AMA with us. I love your focus on people and belief that the right people make all the difference. I completely agree. How do you make your company attractive to the people you want to work for you? Once they are on board, what do you do to keep them engaged and connected to the vision of the company? I ask this question especially in light of the fact that all of our people are now remote. What are your thoughts on keeping a remote workforce with old and new people engaged?

Best regards


Hi Bridget,

Thanks for doing this AMA!

  1. What are those tricks of the trade for bootstrapped startups? 3 pro-tips you’ll like to share.
  2. How quickly were you able to generate revenue? When did you turn profitable and how did you sustain till then?
  3. If you were to start again, what would you be doing to accelerate your path towards profitability?

Hi Bridget,
How long did it take for you to get into growth mode? What are the challenges you faced due to bootstrapping?


Hey Bridget,

So glad to have you on Relay!

You mentioned something fascinating in your interview with Jane Portman. That there’s a distinct stack for the free YouCanBookMe product and in some ways you treat that offering as a separate business unit.

I’m curious to learn how deeply this distinction runs:

— How does it play out when it comes to customer feedback loops and product ownership within the team?
— Does this mean, you also forgo the traditional freemium funnel? If so, how do you measure success, what are the metrics that matter?


Hi Bridget,

Thanks for doing this!

Loved your BoS talk! Wonderful take on how to build a culture.

A couple of questions:

  1. Given that you operate in fairly competitive space with several free products and also a dominant competitor in Calendly, how did you go about deliberately positioning the company/ product in the mind of your users as a differentiated product compared to competition.
  2. As a bootstrapped company what were your marketing channels (apart from the free version). Content - which most self serve/ bottoms up saas companies seem to invest in - does not look like it is a big focus for YCBM. Is that accurate and deliberate ?

Hi Bridget,

Thanks for doing this AMA.
What are your inputs on maintaining the team morale in tough situations like what we are currently in - globally?

Logesh G


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,