Start-Ups – Andrew Essa

Legaltech Venture Investment

This week Crunchbase produced some numbers covering Legal tech investments in 2021.

Legal tech companies have already seen more than $1 billion in venture capital investments so far this calendar year, according to Crunchbase data. That number smashes the $510 million invested last year and the all-time high of $989 million in 2019.

While dollars are higher, deal flow is a little behind previous years, with 85 funding rounds being announced so far in 2021, well behind the pace of 129 deals last year and 147 in 2019.

Some of the largest rounds in the sector this year include:

San Francisco-based Checkr, a platform that helps employers screen job seekers through initiating background checks, raised a $250 million Series E at a $4.6 billion valuation earlier this month;
San Francisco-based legal services provider Rocket Lawyer closed a $223 million venture round in April; and
Boston-based on-demand remote electronic notary service Notarize raised a $130 million Series D in March at a reported $760 million valuation.

According to various start-up founders:

“This mainly is a paper-based industry. However, COVID exposed inefficiencies and it forced people to look at everything you do and explore new ways.”- Patrick Kinsel, founder and CEO at Notarize

“There’s no doubt COVID provided huge tailwinds for legal tech growth,” said Jack Newton, co-founder and CEO at Vancouver-based legal tools platform Clio, which raised a $110 million Series E at a $1.6 billion valuation. “It was the forcing factor for firms that had put off their transformation.”

“Since the midpoint of last year, we’ve seen an acceleration of our business,” said Vishal Sunak, co-founder and CEO at Boston-based management tool developer LinkSquares, which used that increased interest to help raise a $40 million Series B in July.

Here are a few observations on what is going on:

Impact of the Cloud: Just as in many industries, the cloud and other new tech had been slowly changing the legal world for more than a decade. However, after COVID caused offices to close and legal processes and documents to go virtual, adoption of those technologies skyrocketed. Investors started to eye technologies that took many firms “in-house” processes and moved them to the cloud—many involving documentations and filings as well as tools to help better communicate with clients.

2. Cloud-first generation: Many general counsels are now coming from a “cloud-first” generation and know the importance of things such as data insights that can help predict outcomes. Just as data and AI has changed marketing, sales and finance, the legal community is now catching on, and many don’t just want to be a cost centre

3. Increasing investor knowledge: The increasing market and scaling legaltech start-ups are causing VCs to take note. While many investors eyed the space in the past, more investors have knowledge about contracts and legal tech, and founders do not tend to have to explain the market

However, the market is still small albeit growing and no ‘goliaths’ exist in the space. With no large incumbents, how investors see returns remains a popular question.

This may chance if, for example, horizontal software companies like Microsoft or Salesforce could become interested in the space—as legal tech has data and analytics those types of companies find useful, Wedler said.

Some companies in the space also have found private equity a viable exit, with films like Providence Equity rolling up players such as HotDocs and Amicus Attorney several years ago.

However, perhaps more interesting to some startups is the legal tech space even saw an IPO this year, with Austin, Texas-based Disco going public on the New York Stock Exchange in July. The company’s market cap now sits at $2.8 billion.

One thing most seem certain about is that while the legal world’s tech revolution may have been brought on by a once-in-a-century event—there is no turning back.

Evaluating Your Business Idea With Better Customer Discovery Questions

As someone who is fascinated with start-ups and business ideas, I loved this post called “100 Questions You Can Ask In Customer Interviews”.

In it, the author compiles an inventory of questions you might need to better understand the problem you are trying to solve for the customer, how important is it for them in the context of their life, how they currently solve it (or not), and so on.

Having founded start-ups and advised many other founders, it still surprises me that many people do not take the time to do this work to the quality and depth required. Many do not even know about it or value its importance, which really baffles me. Obviously it is more ‘exciting’ to get on with it and ‘start building’, although this is fraught with serious risks.

In any case, the tool above is certainly a great way to have better conservations with potential customers and shape propositions accordingly.

A Quick Course on Lean

Today I came across a brilliant resource from Steve Blank for anyone interested in better understanding ‘lean’. It covers resources helpful for a formal class or for anyone who wants to review the basics. Here is what he provided:

The Harvard Business Review Article “Why the Lean Startup Changes Everything” ties the pieces together here

The Mission Model Canvas

What is the Mission Model Canvas

The Mission Model Canvas Videos

Extra’s

Why Customer Development is done by founders

What Do Customers Get from You?

What are Customer Problems/Pains?

Users, Payers and Multi-sided markets

How do I Know I Have the Right Customers – Testing

How big is it?

How to Avoid Pricing Mistakes

More two-minute lectures here

Tools for educators here

Tools for students here

Understanding Value Proposition

Last week I posted here about my experience mentoring a start-up team from LSE’s Innovation Accelerator programme.

This week I have asked the team to get more ‘granular’ to better define, understand and analyse the problem they are focused on solving i.e. identify user pain-points, challenges, jobs to be done.

In the original Uber pitch deck the co-founders demonstrated a good understanding of the problem for the different stakeholders. Once this is done to a satisfactory level, you can then start to ‘test’ with customer research, experiments and MVPs.

To assist the team, below I provided some great videos from Strategyzer

The Value Proposition Canvas Explained
Value Proposition Canvas: Best Practices
The Basics Of Testing Business Ideas

Customer Discovery & Development

Last week I began mentoring a team who have entered the London School of Economics (LSE) Innovation Lean Accelerator Programme.

Team’s need to focus on improving their Lean Canvas which initially requires an in-depth understanding of the problem they are looking to solve.

This process of ‘customer development’ or ‘discovery’ is probably the most vital phase of a start-up’s life. However, in my experience advising would-be founders, it is often the least understood area of start-up development.

There are many reasons for this, but far too often I find that budding entrepreneurs are not willing to ‘get out of the building’ and talk to potential users/customers in the right way. And do this in an iterative and ‘lean’ way over time.

To help my team to better understand the process, I shared with them these resources. Whilst not comprehensive, provide a good introduction to better understanding and defining the problem (and most critically, how important it is for that user in the context of their life/work).

TechStarts Toolkit

Conducting Customer Discovery Interviews

Neil Patel 26 Customer Discovery Resources

Steve Blank Lean Launchpad Videos

Steve Blank Start-Up Tools – (focus on the Customer Discovery section)

If you come across any other interesting resources, please share in the comments or on twitter @andrewessa

Don’t Think You Have To Conquer The World Straight Away

Today I came across a video from 2014 from The Happiness Start-Up School Summercamp where I was interviewed about starting a business, inspiration, and other entrepreneurial things.

At the time, I was 2 years in to launching The Social Experiences Club, one of the first online marketplaces for connecting people with experts and hosts for unique experiences and activities.

If you can ignore the amount of ‘ums’ and ‘aahs’ I unfortunately use, it does provide interesting insight into my thinking whilst in the thick of start-up mode.

How Airbnb Cut 25% of Its Workforce

Every day we have been witnessing examples of great leadership (or not so great). On its face, the approach to layoff 25% of Airbnb’s workforce – which until the crisis was on track for a bumper IPO – seemed like another one of those great examples.

However, the coverage has been both supportive and negative. Without going into the detail of it, my initial thoughts are that if there was ever a ‘classy’ way to do this, this was it.

You can read the full statement from CEO Brian Cesky here and judge for yourself.

HelloFresh

It’s an exciting day today. Our weekly HelloFresh order of 5 tasty meals for the week has arrived..

Prior to lockdown we had started to experiment with HelloFresh. Perhaps a few meals per week every few weeks. Any service which can make preparing tasty, healthy meals easier and more convenient for busy parents will be a winner. Especially in a location (Guernsey) where online food delivery is very limited.

Since lockdown, we are now power-users moving to 5 meals per week, every week. I doubt this will continue, but for now it is our treat given that we can’t easily access supermarkets, restaurants or bars.

The Challenge for Video-Conferencing Vendors

Yesterday I participated in a 4hr virtual symposium called ‘Disruption 2020’ run by the MIT Sloan Management Review. If you are interested in disruptive innovation and strategic management, this was a brilliant session with experts including Scott Anthony (Innosight), Amy Webb (NYU Professor and Founder, Future Today Institute), and Rita Gunter McGrath (Professor, Columbia Business School).

They have an edition dedicated to it which you can see here.

The VC session was run on GoToWebinar, one of the traditional VC incumbent firms founded in 2004. Unfortunately, the technology didn’t work that well. If I had to rate the user experience of the technology on a scale of 0-10, with 10 being perfect, I would give it a 5.

Every speaker and host (there were 8 or so speakers and 2 hosts) had issues. One had to drop out then come back in. A few speakers could only speak as the VC wasn’t working. Some had constant cutting out or freezing throughout.

It is unclear why these issues were occurring, and who exactly is responsible. Whether it is GoToWebinar, internet bandwidth, home wifi, 4G, human error or something else, this shouldn’t be an issue in 2020. For me, this feels like what dial-up internet was in the early 2000s.

Clearly these are the fundamental CX issues which have enabled a young start-up (Zoom) to rapidly scale across B2B and B2C with a powerful value proposition focusing on the B2B SaaS Playbook: ease of use, integrations, free or flexible pricing, and better performance. I wrote a post recently on how impressed I was a few months ago in being able to easily host a global conference hosted by Seth Godin with many hundreds of people.

Whilst Zoom is facing other challenges right now (e.g. security, privacy etc), from what I have seen with competing vendors, it will be around for a long time to come (and the others, won’t be).

Strategy Tools

Recently I came across Strategy Tools and the founder Christian Rangen. He has put together a series of simple tools and software to make it better, easier, and more fun to think about, and develop, strategies and plans within businesses large and small. There are multiple ways to use the tools, whether in-person or virtually via canvasses, simulations, games, apps, and more.

There are many other use cases for the tools (e.g. government, executive education etc) however the point is well made: the practice of strategy has become too hard.

As a strategy practitioner and consultant for over a decade, he is 100% right. Why this is the case is a post for another day.

For example, the below ‘Strategy Intro’ tool is visually, super simple. The hard part is obviously getting the details filled out. But having an easy way to represent something complex – in a way a teenager could understand – is a huge benefit for firms and practitioners.

This is especially relevant for those firms who believe that ‘strategy’ is spending 6-9 months every 3-5 years to create a 300 page document full of power-points which no-one ever reads, nor can remember.

There are 30+ more of these tools available for different business requirements (e.g. scale-up planning, transformation). Over the next few weeks I’ll be learning from Christian (via the Strategy Tools Coaching Course) deep-diving into these. I’ll be sure to write a few posts on how it goes, as well as the most relevant tools I come across.

Reed Hastings

As part of the 30 Disruptive Leaders in 30 Days Challenge that I set myself here, today I provide some insight around one of the best examples of a disruptive leader in Reed Hastings, CEO of Netflix.

If there was one word to describe how he demonstrated disruptive leadership, it would be this: Courage

Courage (noun)

the ability to do something that frightens one; bravery.

“she called on all her courage to face the ordeal”

Why?

For almost a quarter of a century, Netflix and Reed Hastings have been in a constant stream of business wars, technology paradigm shifts, business model innovations, consumer habit changes, and multiple economic crashes. Despite this, Netflix has not only survived this chaos with Reed at the helm, but on multiple occasions, come out on top (as at April 2020).

A few examples of courageous (or, audacious, bold, daring, fearless) decisions made by Reed and Netflix during this time include:

Decision to bid $100M (at the time a significant chunk of revenue) to win House of Cards from cable rival HBO in 2011, and launch a risky backwards integration strategy into original content production;
Decision (2007) to open up its recommendation algorithm to the public and offer $1M to anyone who can improve it by more than 10%

However, it was the game-changing decision in the mid-2000s to pivot the company to invest and scale a streaming model which I believe was the most significant. To execute, the company split into two business units and the management team of the DVD business – at the time representing 95% of revenue – were allegedly told by Reed to stop attending Netflix senior management meetings (see CNET article here).

Reed explains his thinking below:

“For the past five years, my greatest fear at Netflix has been that we wouldn’t make the leap from success in DVDs to success in streaming,” Hastings wrote. “Most companies that are great at something – like AOL dialup or Borders bookstores — do not become great at new things people want (streaming for us) because they are afraid to hurt their initial business.

“Eventually these companies realise their error of not focusing enough on the new thing, and then the company fights desperately and hopelessly to recover,” Hastings continued. “Companies rarely die from moving too fast, and they frequently die from moving too slowly.”

4 Resources to Learn More About Reed’s Leadership:

CNET article (2012) – A brilliant inside look at what happened during Netflix’s 2011 price-hike crisis which cost it 800k subscribers and stock to crash 77% in 4 months. A few leadership learnings from Reed are below:

Do not underestimate the need to manage different businesses separately;
Be forthright and transparent with customers at all times
Take responsibility, quickly.

TED Interview with Chris Anderson (2018) – A great interview which goes deep into Reed’s leadership style, decision-making, and ethos. According to Reed:

‘…courage is a value which must permeate the organisation. employees to have the courage to speak their mind as otherwise ‘to disagree silently is disloyal. You need the debate but it is not intense; it is more curiosity, to draw people out…’

Netflix Culture and Philosophy – This has been codified on its careers site. Once you read this, you are not left to any doubt as to why Reed – and Netflix – has been able to successfully lead the firm through disruption. More than once.

Reed’s Top 10 Rules for Success (see below). This is a compilation of advice from various interviews Reed has conducted. It is nicely put together. Key themes are :

Be Authentic
Edge of Chaos
Create Joy
Known Your Mission
Be Honest
Keep Improving
Think Long Term
Focus
Strong Values
Patience

Zooming

I came across an article this week here which asked whether Corona Virus (CV) could present a tipping point for virtual events. This reminded me of a pre-CV experience at the end of 2019. I attended a virtual conference hosted by marketing guru Seth Godin.

Afterward I was amazed at how far VC technology has come in being able to easily manage large numbers of people in an interesting and organised way which adds-value to both sides. He ran it using Zoom, had over 300 attendees from 50 countries, used self-managed break-out rooms over the course of the 2hrs, and created interactivity (which game them market research) with Q&A into the chat boxes.

Whilst it wasn’t perfect, it was impressive. I would certainly attend more of these, and reconsider in-person ones. Until this time, I had only ever used VC tech for standard corporate meeting use cases with just a few people. Now, I am recommending my parents to set up Zoom as an alternative for traditional B2C options (Skype, FaceTime). Although that may change if the firm can’t get a handle on Zoom-bombing.

Despite some negative scaling side-effects and challenges, Zoom’s stock has post-IPO gone through the roof (actually, through the atmosphere). This gives them a massive window to place new bets and scale-up new products, value-added services, and M&A.

It is not often a newly public firm gets to invest for the long-term, but now is the certainly the time to accelerate investments into becoming a key player within the enterprise (and B2C?) ecosystem. Vertical, horizontal and hybrid platform solutions across many sectors and use cases will likely emerge as it has with IoT. It will be interesting to see how it plays out, how Zoom responds, and how long until its market capitalisation falls back down to earth.

Understanding Product-Market Fit

“The term product/market fit describes ‘the moment when a startup finally finds a widespread set of customers that resonate with its product” – Eric Ries

I’m currently advising the management team of a multi-national technology client who are looking to commercialise a B2B SaaS platform they acquired recently. The software isn’t a standalone product so doesn’t have market traction nor product-market fit (PMF). Whilst a plan to achieve PMF is critical, a more immediate task is to educate the management team on the actual concept. I’ve discovered recently that it isn’t a commonly understood term within the client, although the high-level meaning behind it is.

From my start-up days, the concept of product-market fit (PMF) is firmly engrained into my way of working (and thinking). Before that experience, I hadn’t come across it. I had forgotten that PMF within corporates probably isn’t an assumed way of understanding product development.

To help me plan and educate the client, I did a deep-dive into the research for articles. The best one is a brilliant summary from Tren Griffin reposted on the blog of Silicon Valley VC Andreesen Horwotiz. It is so good that I needed to share it here. It’s a must read for anyone working in business today.

The Hype Cycle

I came across an article today which talked about why IoT has fallen short of expectations (check it out here). In summary, the key themes were:

Optimism of prediction
Niche consumer value
Privacy concerns
Inconsistent standards across hardware/software
Costs and limitations
Slow promise of the smart home use case

Reading this reminded me of what tends to happen with the adoption of most disruptive (or new) technologies, whether the Internet, AR/VR, AI, blockchain, or cryptocurrency. It is best represented by the Hype Cycle for Emerging Technologies who shows the rise-fall-rise of how markets tend to adopt innovations.

Below I’ve pasted in a Hype Cycle dedicated to IoT:

The key takeaway from the above charts is time. People always overestimate how quickly the mass market will adopt new innovations. There’s an entire body of work dedicated to explaining the reasons and not for this post. But it’s just not easy to get technology to a cost/performance level that works beyond the early adopters. A lot of things have to go right. And that includes one of the biggest things beyond technology: changing human behaviour.

Interview – Lance Plunkett

One of the first people I met when moving to Guernsey was a fellow Australian called Lance Plunkett. He was in the early stages of MVP development for his lost property start-up Found. I thought it would be a good idea to get to know him better and help me flesh out my developing theories around ‘start-up thinking’. I compiled some questions and shared it with him via email. Lance was good enough to provide great responses, so below is is what I received back:

What is your start-up? It’s called Found. We are a funky, agile and innovative start-up aiming to become the known brand in lost property, so that if someone ever loses or finds something they immediately turn to Found. We are leveraging the Found network of businesses and individuals to offer various insurtech products, which fit perfectly into the world of lost property and allow users to protect their valuable items. We are exploring utilising blockchain technology for proof of ownership and fraud prevention purposes.

Why do you pursue this path vs something else? It’s a really big challenge and I love challenges; for me life is about really going for it and pushing and challenging yourself in everything you do.

Why do you think you are (or will be) good at it? I know where my strengths and my weaknesses lie which enables me to identify the people I need around me in the team to pick up on the areas I am not so good at! Being a founder is a tough and lonely journey at times so having people around to help support, motivate, complement your skills, focus and enjoy the journey is important.

As I see it, one of my key skills is being creative and innovative in problem solving I really enjoy this process. I am very willing to listen to and learn from others so that I can develop my own skills, self analysis and being honest with yourself and your own performance is important you have to be able to take criticism from others and I am good at this.

I am prepared to make sacrifices to make this happen I worked for a year on my business earning no money and living on a boat!

For me personally one of the keys to success is building relationships; relationships with investors, clients, customers and your team. It’s important to be personable, honest, human and considerate to others – these are hugely important values to me.

I really believe in what I am doing and share that belief and passion with others.

What does ‘entrepreneurship’ mean to you? For me it’s about being creative and innovative in solving problems and finding better ways of doing things.

What do you consider to be the ‘start-up mindset’? Which do you think are the most important for start-up success? Please explain with any relevant examples. I have met many successful business people/entrepreneurs; some are great visionaries, some are great creators, some are crazy, some are straight-laced and some are great with numbers BUT the one common thing amongst them all is their commitment and determination to their business or idea. The start-up mindset is about commitment to your goals and conviction in your business. I had the idea to solve the problem of lost property three years ago and have kept working on it and have maintained a true belief in it ever since which I know will see it through to success.

I liken my approach to business to the first time I went skiing. I learnt as an adult and went to the slopes with my three best mates, all of whom could ski really well. I remember thinking ‘Right, what’s the quickest way to get good at this so I can ski with them and not get left behind?’ and I concluded that it was by teaching myself on the most difficult black run! Charging head first into many big crashes, I got up and went again and again. I did learn very quickly and could ski down that black run in no time. It was a riskier approach but one that I calculated was worth it and that I could achieve — the rewards were big – I could ski with my best mates! Throwing yourself with commitment and passion is important and I certainly try to do this in life and business. As an entrepreneur you have to take risks however the risks I take are certainly calculated and thought through.

What are the different ways you have used to develop or improve such attributes? (If helpful, refer to any practical tactics, tools, habits, experiments or other useful strategies) I read a lot about successful people and how they do things. I study the characteristics and behaviours of sportsmen, coaches and entrepreneurs. I am very observant of others around me and how they behave, and learn from mentors, friends, peers and family.

How has a failure, or apparent failure, set you up for later success? Do you have a favourite failure? Learning how to fail and how to lose is a key to growing as a person. I played professional football for many years at a high level but failed to reach the very top level. I had the opportunity but didn’t really commit myself, as I should have. I have certainly applied the lessons I learnt from that to my business life now. Learning from previous mistakes would be in my top five tips for success!

When you feel overwhelmed or unfocused, what do you do? (If helpful, what questions do you ask yourself?) I find being healthy mentally and physically helps and if it all becomes too much a good walk with the dogs in the fresh air can help clear the head. I am good at dealing with stress and tough situations. Talking through my business problems with those trusted colleagues, friends and family is really important.

In the past five years, what new belief, behaviour or habit has changed your life?For me personally I was very immature and unfocussed for many years. I loved that part of my life and don’t regret it for a second – it was fun and I learnt a lot! But I now feel a new maturity and confidence in my skills and have the focus and ability to channel those skills into something I really believe in.

Where do you derive creative inspiration for new products / services? How do you put it into practice? I naturally look at processes/the way things are done and am always imagining what I could do to make that process better. I think of new businesses or ideas to solve problems daily. Looking at new technologies is fascinating and a great way to see how they can help make things better, safer, cheaper, faster etc.

What is your approach to managing risk? Please provide any example(s), if relevant. I take risks everyday as a business owner but they are calculated risks, all decisions are carefully considered, researched and discussed with others when needed. Surrounding yourself with good people minimises risk and I try hard to do that.

How do you know when it’s time to pivot, change direction or quit? Please provide any principles, tactics, criteria etc. I think this is easy to identify – needs must type thinking. If you are set up as a lean agile business change should be easy.

What advice do you have for your 20yo self about to enter the ‘real world’? What advice should they ignore? I wouldn’t want any advice or change a thing, the mistakes I have made are all part of learning and growing.

Are there any quotes you think of often or live your life by?

There are no wrongs or rights in how to become successful; there are many paths to where you want to go.

Success takes all shapes and forms – it doesn’t necessarily mean how much money you have.

Be humble, kind and considerate to others.

Always listen to others’ advice – you can pick up teachings from everyone you meet even if it’s ‘that’s not how to do it’!

Take the road least travelled.

What are the books that you most recommend or gift to other people?

I like Richard Branson’s books they are fun, honest and an easy read with some great lessons within.

Why Start-Ups Fail

I came across this infographic recently. It made me grin. As I’m a few years passed my own start-up failure, I can now chalk it up properly as lessons learned.

See the source image

Looking at the list, the scary thing is that just about all apply to my experience. The only ones that don’t apply are passion/burn-out (although the final year 4 was tough), poor marketing, ignore customers, location, & legal issues. Everything else was a contributing factor. Now, that’s a heck of a lot of (expensive) mistakes to make. I was in control of most of them as well. So it’s not as if I can shift responsibility to others. The buck stopped with me. So what happened? At the end of the day, I just didn’t have the product-market fit piece understood, let alone nailed. The words of Marc Andreesen (founder of Netscape turned VC) sums up nicely what was (or wasn’t) going on:

“You can always feel when product/market fit isn’t happening. The customers aren’t quite getting value out of the product, word of mouth isn’t spreading, usage isn’t growing that fast, press reviews are kind of ‘blah’, the sales cycle takes too long, and lots of deals never close. And you can always feel product/market fit when it’s happening. The customers are buying the product just as fast as you can make it — or usage is growing just as fast as you can add more servers. Money from customers is piling up in your company checking account. You’re hiring sales and customer support staff as fast as you can. Reporters are calling because they’ve heard about your hot new thing and they want to talk to you about it. You start getting entrepreneur of the year awards from Harvard Business School. Investment bankers are staking out your house. You could eat free for a year at Buck’s.” – Marc Andreessen

Introducing Start-Up Thinking

Since exiting the start-up I founded in 2011, I’ve been thinking a lot about lessons learnt. In particular, what were the ways of thinking, working and operating that helped me ride the roller-coaster that is entrepreneurship. Here is the initial list I came up with:

Curiosity
Creativity
Agility
Vision
Grit
Experimenter
Ownership
Tenacity
Failure
Innovative
Collaborative
Constraints
Confidence
Risk

Looking at this list, it begs the questions. Why is it important? Can anyone learn or develop these attributes? What principles, tools & tactics could someone follow to improve work and life? Should these be the future talent management model companies should instead focus on?

Clearly, in this day and age the pace of change is more significant than ever. Established firms typically do not have the agility to respond & most talent management frameworks are likely still aligned with old ways of working & operating. It certainly would be an interesting study to see the results if recruitment & training focus shifted to some of the attributes outlined above.

But can anyone learn or develop these characteristics? Of course they can. I certainly did. And so did the millions of start-up founders & entrepreneurs that came before and after me. I’ll do some digging on this and blog about it here over the coming weeks.

The Art of Customer Development

I recently crossed paths again with an excellent summary (from Mike Fishbein – link below) of key questions when developing a new product or exploring improving an existing one. It reminded me of how useful it was to be validating a potential new product idea back in 2013.

At that point I was desperately seeking a new product to hopefully facilitate a do-or-die pivot of my failing activities & experiences marketplace start-up (The Social Experiences Club). Although we had launched in 2011/12, it wasn’t on the back of much customer insight and their problems, needs, challenges etc. In fact, it was based on a tonne of assumptions. Some of these were tested (off-line by running a specific live experience/activity with paying customers), but the wider product concept (central place to discover and book all sorts of experiences) was not.

Back then there wasn’t a ‘handbook’ on running a start-up in the Internet/mobile era or properly managing customer development or producing tangible evidence of why the problem you’re solving is such a major problem for a big addressable market. Lean Start-up was only in the very early stages of traction and certainly no-one in London was talking about it. In hindsight, that lack of customer insight was one of the key reasons (and there were quite a few) for eventual failure.

In 2018, there are now a significant number of free (or cheap) online resources & services at the disposal for any budding entrepreneur to test, validate & build MVPs for that side project or next big thing. What an amazing time to be around and have an idea. The same old challenges remain however: to (a) find and solve a problem that is important enough to a significant number of people, and (b) stop watching Netflix in your spare time & get out there and work hard to find out if your idea has legs. Check out the questions below with thanks to Martin Fishbein

Customer Segmentation
Depending on how you obtained the interview/how much background you have on the person, you may need to make sure they are within your customer segment, and/or understand more about their demographic. I usually try to keep it to a max of three.
What do you do professionally?
Who handles [process you’re improving] at your home/office?
Tell me about your role at [company]?
How much time do you spend on [process you’re improving]?
[Specific questions related to your product/customer] – for example, do you have kids?

Problem Discovery
Questions to validate your hypothesis about a problem, or to learn about problems.
What’s the hardest part of your day?
What are some unmet needs you have?
What product do you wish you had that doesn’t exist yet?
What tasks take up the most time in your day?
What could be done to improve your experience with [process/role]?
What’s the hardest part about being a [demographic]?
What are your biggest/most important professional responsibilities/goals?
What are your biggest/most important personal responsibilities/goals?

Problem Validation
If your customer did not talk about the problem you wanted to address, use the below questions to begin validating/invalidating that your customer has the problem you think they have. In addition, it’s often not enough to just solve a problem, sometimes it also needs to be one that people are highly motivated to solve. Some of the below questions can help with that too.

Do you find it hard to [process/problem]?
How important is [value you’re delivering] to you?
Tell me about the last time you [process you’re improving] – listen for complaints
How motivated are you to solve/improve [problem/process]?
If you had a solution to this problem, what would it mean to you/how would it affect you?

Product Discovery
Questions to help generate ideas or to validate your idea. The below questions are intentionally very open-ended. By asking yes or no questions specifically related to your product, customers may feel inclined to agree with you or not be critical. By asking more open ended questions, you can be more confident that they’re giving you honest input. If in response to the questions below, your customers tell you they’re looking for similar to what you have in mind, you might be on to something.

What do you think could be done to help you with [problem]?
What would your ideal solution to this problem look like?
If you could wave a magic wand and instantly have any imaginable solution to this problem, what would it look like? – I’ve found that about 80% the time the answers I get to this question are not very informative – solutions that aren’t feasible or most certainly wouldn’t be profitable. But the other 20% of the time there are some really informative responses that make the other 80% acceptable.
What’s the hardest part about [process you’re improving]?
What are you currently doing to solve this problem/get this value?
What do you like and dislike about [competing product or solution]?

Product Validation
Questions to validate/invalidate your idea.
What do you think of this product? – this question is intentionally vague. Listen to whether they talk about wanting to use the product or how it could be improved. Given how vague the question is, the former is positive, while the latter may be a sign that improvement is needed.
Would this product solve your problem?
How likely are you/would you be to tell your friends about this product?
Would you ever use this product?
Would you be willing to start using this right away?
What might prevent you from using this product? – might reveal ways that you could improve the product. Potential hurdles might be budget, time, perception’s of the product’s value, a competing product, etc.
Will you pay $x for this product? – see if they will put their proverbial money where their math is. Often times when you ask this question, no matter how small the price, you will start hearing key insights that you wouldn’t have heard otherwise.

Product Optimization
Questions to help you improve your idea or product.
What could be done to improve this product?
What would make you want to tell your friends about this product?
What’s most appealing to you about this product?
What might improve your experience using the product?
What motivates you to continue using this product?
What’s the hardest part about using this product?
What features do you wish the product had?

Ending Interviews
Questions to ask at the end of an interview. You may also need to ask for their contact information if you don’t already have it.
[Summarize some of your key takeaways] – is that accurate? – I usually do this throughout the interview.
So based on the conversation, it sounds like x is really hard for you, but y is not. How accurate is that?
It sounds like x is very important to you, while y is not. How accurate is that?
Is there anything else you think I should know about that I didn’t ask?
Do you know anyone else who might also have this problem that I could ask similar questions to? – small form of validation if they’re willing to give you referrals
Can I keep you in the loop on how the product develops?
Can I follow up with you if I have more questions?

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Lean in Context

The Business Model

How to Get Out of the Building and Test the Business Model

The Mission Model Canvas

Extra’s

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