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Storytelling boost: how to do a pitch workshop with a startup, using 10/20/30 rule and design thinking

Storytelling boost: how to do a pitch workshop with a startup, using 10/20/30 rule and design thinking

Clarify your vision and simplify your communication to empower internal alignment and improve sales & fundraising processes

Pitch workshop 101

Every startup needs a powerful story
For two big audiences: internal and external. Internally, actual and future employees need to feel the power of the overall vision, being happily driven by that. Externally, both customers and investors want to understand as much as possible all the value generated by the company. 

For these reasons, every startup chief or decision maker should pay huge attention on storytelling. It’s an amazingly versatile tool: it works both as strategic map and as marketing enhancer. 

In this post I’ll share a workshop, made remotely using Whereby and Miro in late 2020, with startup team. They were looking for some team building support, a common story to converge together and a boost on their investors pitch. 

We’ll see how a three people team, supported by a facilitator, can diverge and then converge on the business vision in a 4 hours morning session, taking away a story backbone able to drive their upcoming pitch decks. 

Clarify your vision and simplify your communication to empower internal alignment and improve sales and fundraising processes

Business context and target audience

Shared Media is a tech startup dedicated to ease the process of sharing digital memories, based in Trento, in the north east of Italy. Born in 2017 and funded with € 60 K by the European Union through Trentino-Alto Adige region, they faced an explosion in their service during summer 2020. 

Shared Media has 2 cofounders and 1 lead developer: Marco SoaveIT engineer with research background on AR/VR, Nicolò Paternoster, software engineer with previous startup experiences and Andrea Cavattoni, software developer with 11 years of freelancing background. 

After a LinkedIn connection with Marco, he told me they were significantly growing revenues after onboarding one client that was using Shared Media solution with great results. 

This proved them their product was cool and the business model was interesting: now they understand that is time to go out of the building looking for new customers like this. 

But like any respectable startup looking to scale, they can’t rely on internal money, so having in mind to fundraise successfully in the next months, they feel is the right moment to start building a powerful storytelling. 

Following there is their explainer video now on website’s homepage, made in August 2020. It’s in Italian, but you may understand generally speaking what we are talking about, having also a taste about the team’s communication potential. 

Short story of the service

The product is a SaaS able to receive in input any video source and output a nice edited highlight of 2 minutes length. Their favorite target audience are extreme sports activities, who have dozens customers per day interested to have a memorable experience. They offer to these companies a B2B end-to-end service, able to provide hardware needed to record their customers; then the software do the magic, extracting an awesome short version of the recording and sending to people a digital drive with their content, easily shareable with friends and onto social media.

By October 2020, their KPIs are more than interesting: with 1.5K registered users on the website, they have published more than 5K experiences. The average unique visitors per month in the app site are around 30K, usually visiting the site twice. This means two things: first one, the service is reliable and capable to show already thousands of well performed “cut’n’share” activities; second one, people love it! Every experience is seen on average by 6 different people a couple of times. 

Without any doubt, Shared Media has all the ingredients to bake a tasty story.

(Below screenshots from the Shared Media platform, where users can enjoy their personalized content)

Screenshots from the Shared Media platform, where users can enjoy their personalized content

4 tips to prepare for a pitch workshop

  1. First of all, involve a facilitator. Having an external look on your everyday activities is crucial to get rid of as much biases as possible. Sometimes doubts that are freaking your mind since months can be clarified with a savvy professional mastering the right frameworks 
          1. Then invest some time to share with facilitator the right amount of information. Not too much, not too few: s/he must listen your story, understand your service, know your audience and see your goals


            1. Finally when you feel there’s a fit with the professional and you’ve shared adequate knowledge on your business, take the lead with your colleagues. Setup a table involving from 2 to 6 decision makers from your team, tell them why your startup needs to do this activity, what are the deliverables you’ll take away and why the professional you’ve selected is the right one to support you in the process


                1. Book on everybody’s calendar sufficient timing to be together at the same table, physical or virtual doesn’t matter, be prepared to exit your comfort zone being challenged by a stranger and remind your team mates to do the same 
                Clarify your vision and simplify your communication to empower internal alignment and improve sales and fundraising processes

                How to perform a pitch workshop

                The facilitator will drive you through all the process. I’ll tell you here how we designed our morning, with a 4 hours full immersion session.

                9am -> 10am
                : introduction and company vision 

                It’s important to start with a soft approach, as the session is quite disrupting. We started presenting ourselves, sharing a bit of our backgrounds and own expectations for the day. Then my question was quite simple, “What is Shared Media for you?”: from here the team made a 5’ each free talk, speaking out their opinions on the business, customers, business model, revenues, potential, kpis, fundraising, weaknesses and next goals. Meanwhile, I was drawing on Miro’s post its synthesis of their thoughts color coding them while they were speaking. 

                Clarify your vision and simplify your communication to empower internal alignment and improve sales and fundraising processes

                The result was amazing: after 15’ we had an overview of the startup from every team member angle, color coded to facilitate an overall understanding of their unconscious priorities perception. While the opinions itself were pretty similar, the order everybody used to highlight concepts in their stories was very different, as you can appreciate from the image above. The team was pretty impressed by this approach, underlining the potential of this teamworking framework and wishing to dedicate time to activities like this regularly, since is usually hard to reflect together on these sensitive topics. 


                10am -> 11am: analysis of actual pitch 

                After the introduction, where everybody was made comfortable with the context and immediately felt the potential of the session, we went through the main topic: the pitch deck. So we started overseeing the old deck they made (Italian version below). 

                Then we made another roundtable to let everybody share their thoughts regarding the actual version of the pitch. For me as facilitator, this was really helpful to understand what they liked of the previous version and what they really wanted to change as a team. For them this was helpful to discuss together this topic, since usually was covered by just one founder, and openly agree or disagree on mutual opinions into a safe place moderated by an external facilitator. 

                After listening to their point of views, I’ve switched a bit to an advisor role, telling them my personal opinions on the pitch deck. This gave them an opportunity to change their mind over the needs they felt before, also preparing the right mindset to start the creative session later on. 

                Finally I’ve shared them the principles of 10/20/30 rule by Guy Kawasaki, a design thinking framework very useful to build simple and powerful storytelling. You can read more about the technique in this post. 


                11am -> 11.15am: coffee time… 

                …because we’re not machines =) 


                11.15am -> 1pm: design new pitch with 10/20/30 rule 

                We’ve started to follow the 10/20/30 rule framework, with myself again in the facilitator role – but with more knowledge about their business and their mindsets – challenging them to extract a meaningful 3-pillars synthesis of their business for every relevant topic we needed to cover: ProblemYour solutionBusiness modelUnderlying magic/technologyMarketing and salesCompetitionTeamProjections and milestonesStatus and timelineSummary and call to action. 

                At this point, they were comfortable enough with the approach and the context to let the session flow very smoothly: I was there to nudge them when the pace was slowing down, remember from time to time the goal of every block, propose alternative point of view when they were converging too much and suggest simplifications when they were indulging on divergence. In doing this my big concern was the timing, pushing them to accelerate our process forward, and the drawing of every point of convergence in the Miro board. 

                We were able to finish on time with mutual satisfaction and enjoy a small chat in the end =) 

                  Deep dive: previous pitch deck of Shared Media vs. new one

                  Let’s now focus on the differences between the previous deck and the backbone of the new one (Miro board embedded above).

                  Previous one was built on these 


                  1. Problem: traditional digital memories are costly and hard to be shared 


                  2. Opportunity: customer satisfaction, loyalty and free word of mouth marketing 


                  3. Solution: automated video highlight production + sales, distribution, sharing 


                  4. How it works: user login, automated recordings, automated postproduction, sharing service 


                  5. Engineering: 30’ video raw -> computer vision + meta data + ai = 1’ video highlights 


                  6. Value proposition: unique fast emotional offer with high ROI 


                  7. Company vision: create user emotions gently, with high engagement and re-shareable content 


                  New one sounds like this: 


                  1. Problem: people want digital memories and quality is mandatory, but execution is hard 


                  2. Value: sell immortal emotions with sharing scalability and end-to-end automation 


                  3. Underlying magic: effortless workflow transforming 30’ video in 1’, with cloud distribution 


                  4. Business model: upselling on real life experience, with revenue sharing and high margins 


                  5. Market: experience providers, reached through referral cherry picking for win-win partnerships 


                  6. Competition: manual (time & cash consuming); automation + distribution + hardware-less is unique 


                  7. Team: high technical expertise with on field outdoor skills and university collaboration 


                  8. KPIs: 33% selling rate on experiences, with 70% digital usage and 1:10 revenue scalability 


                  9. Next: B2C global reach of SaaS product, detailed case studies and demo setup for trial partners 


                  As you can see, this technical team was helped to move from a tech story to a more wide flow. 

                  This was made in a very short amount of time, aligning all the decision maker in half a day. 

                  The original story was definitely not bad, but it was just incomplete: being so deep in the engineering niche, was not able to put light in every powerful angle of the business. These guys were smart enough to catch immediately the potential of what we made, but even with their great minds capable of building this sophisticated software, it’s surprising how they were not able to communicate the full potential of their vision alone. Analyzing in fact the content of these two pitch decks, in the first one the eye is only on the internal side of the company; in the second one, sacrificing some technical information, the eye is balanced between internal and external point of view. 

                  10/20/30 rule, implemented with design thinking approach, helped significantly to compress the whole workshop in just 4 hours. 

                  Result: a satisfied team recommending fellow founders for the process

                  I wanted to finish this experience not only asking verbally to these guys how much they were satisfied of the morning we shared from 0 to 10, but also giving them a very short feedback form to fill, because I wanted to get rid of emotional bias and to avoid the natural willingness of compliance. 


                  I asked them 5 questions: 


                  1. Your expectations before the workshop 


                  2. How expectations were satisfied [1, not at all – 6exceeded] 


                  3. What you liked about the old pitch 


                  4. How we have improved that today [1, it’s worse – 6it’s ten times better] 


                  5. Refer a friend who could enjoy this workshop 


                  Replies are in Italian so you can’t enjoy from screenshots the quality of their words, but below you can see numeric replies to question 2 and 5.
                  Finally, they recommended two fellow founders that may enjoy like them the entire process.

                  Clarify your vision and simplify your communication to empower internal alignment and improve sales and fundraising processes


                  Summarizing a conclusion for this journey, we can synthesize three macro priorities:


                  1. Enlarge your vision to tell your story is fundamental 


                  2. Being supported in this journey from a facilitator saves you a lot of time 


                  3. 10/20/30 rule + design thinking are unbelievably powerful tools to create this high value job 


         brand was born with the willingness to unlock growth potential for decision makers like Shared Media founders. If you want to know more, check how you fit vision or download whitepaper. 

                  Riccardo Mazzolo

                  Innovation advisor exploring design, storytelling & creativity for growth. Always happy to facilitate people building new solutions to simplify life.