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

[bridget (Bridget Harris)]

@raviramani

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
Ravi

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

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.

2. 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.

3. 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.

4. 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.

5. 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.

[bridget (Bridget Harris)]

@Anushree

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?

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 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!

[bridget (Bridget Harris)]

@ncameron

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,
Neil

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

The Founder’s Dilemma

and that can often be a very personal choice.

good luck - let us know how you get on!

[bridget (Bridget Harris)]

@Jayashree

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

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

[bridget (Bridget Harris)]

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

[astha (Astha Rattan)]

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.

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.

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!

[astha (Astha Rattan)]

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!

[ncameron (Neil Cameron)]

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

[jamesgill]

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

[wingman4sales (Shruti)]

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

[Krish (Krish Subramanian)]

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.

Regards,
Krish.

[rajaraman (Rajaraman Santhanam)]

@bridget

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.

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!