Nick Telson

Founder DesignMyNight (Acquired '19) 🍹 | Co-Founder trumpet 🎺 | Investor in 55+ Startups (Currently not investing in new deals) 😇 | Podcaster 🎙️| 🏳️‍🌈

Hey!

I’m a London entrepreneur, currently living in Boston.  Also an angel investor, podcaster, startup mentor and public speaker, whose speciality lies in talking no-nonsense founder/investor advice and help. I'm currently co-founder of new B2B sales tool, trumpet, host of Pitch Deck podcast and co-founder of an angel investing venture-arm, Horseplay Ventures

I previously co-founded DesignMyNight, back in 2010 and managed to grow that over 7 years with minimal angel funding, to 100+ employees, 15,000 SaaS customers and 8m monthly uniques on the website. We exited to Access Group in 2017.

I live for the early stages of startups - building the brand, finding product market fit, iterating quickly and building out a team. Most of my content is centred around this, as well as tips from an angel investor. Even after exiting to financial freedom, I caught the founder bug again and have co-founded my next startup, trumpet, in 2022; looking to disrupt B2B sales and kill the sales pdf deck. Follow me on here while we build out this new journey in public.

Please feel free to ask for any advice or help, whether a founder, startup employee or investor and I will always endeavour to do what I can. I'm also a regular guest on podcasts, startup speaking gigs and webinars, so feel free to reach out to me if you are looking for guests/speakers. 

I do respectfully ask not to be pitched for investment in my Linkedin DMs and instead go through Horseplay Ventures. Hopefully my podcast is also a treasure trove of information for those looking to raise early-stage investment, thinking about it or just interested in it - search for Pitch Deck by Nick Telson.

Co-Founder

Nick Telson-Sillett

15 years building startups but still managing to have new pinch-me moments 😁 

5 years ago when we were ideating on trumpet 🎺 on a whiteboard, never did I think it would become a billboard on Times Square! 

It may have been -15 degrees but that wasn't going to dampen my excitement to see trumpet flashing over-head in one of the most iconic locations in the US. 

We said we were going big in the States, so why not plant a flag, right?!

Moments like this as a founder are only possible thanks to the team around you and the wonderful customers who took a punt on us, and continue to do so. 🙏 

Immensely proud of what we're building and how we're building it and selfishly allowing me to have lifetime moments like this still

Co-Founder trumpet 🎺 | Founder DesignMyNight (Acquired $30m+) 🍹 | Investor in 55+ Startups 🤑 🏳️‍🌈

After investing in 50+ startups I am more wary of second time founders than first timers.

Sounds backwards, I know. 

I used to think a previous exit was the ultimate green flag.

Then I watched second time founders blow up companies for, what I thought were, very predictable reasons.

A few patterns I look for now:

• They copy paste old playbooks

What worked in a different market at a different time with different capital conditions often falls flat. Playbooks are context not scripture.

• They hire for the company they remember not the one they have

Big salaries senior titles early stage chaos. They forget the scrappy generalists who made their first win possible.

• They overestimate skill and underestimate luck

Timing market structure and competitors all played a part. If you think you were the sole reason it worked you will misread new risk.

• They get bored of doing the unsexy work again

Talking to customers. Manually selling the first deals. Sitting inside product pain. They want to fast forward to PLG as if it just happens.

• They reference their last company more than their current customer

Every answer starts with “at my previous startup we”...I want to hear “this customer told me yesterday” instead.

• They protect their ego more than the truth

First timers ask naive questions. Second timers can be scared to look like they do not know. 

Don't get me wrong I love backing second time (successful) founders.

I just want to see they know this:

Experience is not the cheat code.
It is the library.

The real skill is pulling the right lesson off the shelf at the right time.

A snippet taken from a Solutions Engineer Manager in a joint slack channel with a new customer (2000+ employees and a 6-figure deal) at trumpet 🎺as we began onboarding them.

As well as the very nice things he had to say about us (having looked at all other Sales Rooms during the sales process), for me it shows the huge importance of internal advocacy when kicking off a new partnership.

So many new customers can fall through the cracks between super excited sales cycle to actually onboarding the team. 

Here are some tips before launch to help set up advocacy and context

- Pick an internal owner and three to five champions
One senior sponsor who cares about the outcome
Three to five power users in different teams who are curious and vocal
Give champions early access and ask them to collect rough edges and quick wins

- Sell the problem, not the tool
Run a short internal teaser; what painful thing this will fix
Use one sentence per audience
Put this in every invite and kick-off deck

- Line up specific use cases by team
Do not launch as generic tooling
Create one or two flagship use cases per function that you know work well
Prepare before and after screenshots so people see the difference in seconds

- Remove as much setup work as possible
Pre create workspaces, projects, groups
Pre load example data or templates
Make sure login, SSO, permissions are smooth on day one

You do not build advocacy with features. You build it with the way you roll them out.

Having watched thousands of Pods run through trumpet 🎺, one thing is clear...

The deals that win are the ones that travel inside the buyer

When a Pod gets shared internally by the prospect, win rate jumps from 28% to 56% and when a Pod has an engaged Mutual Action Plan the win rate 2x 🤯 

So we asked a simple question

What if the MAP made those internal shares and engagement effortless? 

That is why we have rebuilt our MAP from the ground up and launched a new experience inside every trumpet Pod

What's new?

• Horizontal progress timeline that shows what is done, what is next, and who owns what

• Automatic nudges to keep everyone on track

• All context and attached docs now live inside the plan, not in scattered docs

• Bulk actions to update the plan easily when plans invariably change

• Calendar view to see zoomed out responsibilities in the month

• New MAP dashboard to see all your live MAPs across all Pods and all overdue and upcoming tasks

The new Mutual Action Plan is live for all customers and already getting rave reviews 🥳 

In the end, the more obvious you make the path, the easier it is for your champion to walk everyone else down it...

When should a startup test, conserve or spend on marketing?
After a being in and around early stage companies, I've seen the patterns.

Most teams are either spraying cash with no signal
or clamping down so hard they never learn anything.

Here is how I think about the three modes.

1) Test mode
Use this when you are still trying to answer basic questions:
• New product or big new feature
• No clear winning channel yet
• You do not really know your payback period

Principles in test mode:
- Set a small fixed pot per channel for a short window.
- Define what success looks like before you start.
- Optimise for learning speed, not for perfect efficiency.
- Kill experiments fast when the numbers are clearly awful.
- If you are arguing for weeks about creative on a tiny budget, you are not testing, you are procrastinating.

2) Conserve mode
This is where more founders should live by default.
Use conserve mode when:
• You have less than 9 to 12 months of runway.
• Your unit economics are not working yet.
• You are between fundraising.

Principles in conserve mode:
- Double down only on channels that are clearly profitable.
- Pause everything that “might work with more time”.
- Shift focus to retention and referrals, not paid acquisition.
- Spend more time on positioning and messaging than on media spend.

Conserve does not mean go quiet.
It means move the energy from ad accounts to customer conversations and product.

3) Spend mode
This is the fun one and also the one that kills companies if mistimed.
You earn spend mode when:
• You have a clear core channel that is already profitable at smaller scale.
• You understand your funnel metrics end to end.
• Churn is under control and customers actually stick around.
• You have enough runway or fresh capital specifically to grow.

Principles in spend mode:
- Increase budget gradually while watching payback like a hawk.
- Invest in brand and content alongside performance, not instead of it.
- Build repeatable playbooks so growth does not depend on one hero marketer.
- Assume the channel will saturate and plan the next one early.

If you go into spend mode before you deserve it, you are just setting money on fire with nicer dashboards.

The real skill is not how much you spend, it is knowing which mode you are truly in and being honest enough to act accordingly.

Anna Liebel ehf.

When your startup seemingly takes over your whole life, how do you stay true to your values and keep nurturing relationships you deeply care about?
When your company is growing, how do you stay sane on that rocketship?
When your success brings more questions than answers, how do you realign to the new insights and deal with them?

My post-grad work experience started within project management in a global engineering company. In the first years of that career, I was often the youngest, the only immigrant, and the only female in the room. I was called "sweetheart" by the seniors who thought they were caring, and an "idiot" by an engineer on my team because I confronted his disrespectful behaviour towards others. On the other hand, I've experienced amazing leaders who were inspiring, attracting talent like a magnet, and getting people to collaborate on amazing levels. I've learned what made a difference in leadership from practice and am on a mission to spread the knowledge so that more companies can thrive, while their leaders feel happy and employees -- fulfilled.

Many leaders feel lonely on their journey. I know it can be another way and am using my strength of creating a safe space, for the leaders to experience a better way of being. Then together, we work on creating that experience for their whole teams, to ensure higher job satisfaction, productivity, good employee retention, more creativity, and generally, better business results.

If you feel like it's time to review and redefine your leadership, schedule a Mindshifting Intensive and let's talk! https://annaliebel.as.me/strategycall

Mindshifter

Reykjavik University

Teaching undergraduate students who major in business or economy at the Business Department. The courses I am partially involved in are Well-being and Critical Thinking, and fully responsible for Leadership and Effective Teamwork.

Lecturer

Managing grants projects, applying for research grants, building collaborations within academia and with the industry, both locally and internationally.

FinTech Research Center Administrator

Designing and leading workshops and courses for the Open University at RU on topics of time management, leadership and communication, DEI, and more.

Corporate Trainer

KLAK - Venture Mentoring Service

Mentor

NUMA

Member of the Numa Coach Academy.

Leading interactive virtual workshops for managers and individual contributors on topics of time and energy management, hard conversations, employees’ and team motivation, delegation and performance, leading 1:1 meetings, hybrid collaboration, asynchronous communication, pitching, emotional intelligence, creativity techniques, and more.

Clients: Richemont (Van Cleef & Arpels, Cartier, Chloé and other brands), Forvia, ManoMano, Kering Group (Gucci, Saint Laurent, AlexanderMcQueen and other brands), Vade, Vestiaire Collective and more.

StartupExperts

StartupExperts is an invite-only community of experienced HR, Finance, and Ops leaders who understand that while we tend to be “teams of one” or leaders of small teams at individual companies, we all regularly encounter the same business challenges and believe that collectively we are stronger when we support each other. As a community of professionals we are passionate about learning, we want to build deeper relationships with our peers, and most importantly we find personal satisfaction in giving to others.

Talent Leader

Stepping Stone Edu

Building and leading the Mentors Network as a part of Stepping Stone Edu's startup incubator. Responsible for creating processes, recruiting, onboarding, training mentors, and ensuring they have a great experience with our team and cohorts.

Additionally, supporting the company's leadership to build a healthy culture and navigate the personal challenges of building a business.

Mentor Network Lead and Leadership and Team Development Manager

National Multicultural Information Center Iceland

One-month assignment for one of the governmental organizations in Iceland, to help them accepting Ukrainians who arrived to Iceland for protection on humanitarian needs. 
Tasks included:
- running information meetings with the newcomers
- holding 1:1 interviews
- preparation of materials for handouts and online resources
- translation services

Assistant to Project Manager

Semcon

Project Management Consultant working with product development and aftermarket.

Consultant

AstraZeneca

As a packaging engineer, I was involved in the new product development and responsible for the choice of suitable packaging for the products, both in the development phase and for the commercial product. Also, been part of the teams developing new inhalation devices.

Packaging Engineer (consultant assignment)

Mölnlycke

During this assignment within global product complaint handlers team, I worked with processing company's product complaints registered worldwide. My duties included initial review and classification of the new complaints, progress follow up with diverse stakeholders including production, R&D and aftermarket, and preparation of customer communication based on the investigations completed within the company.

Global Product Complaint Handler (consultant assignment)

I help entrepreneurial leaders and their teams stay sane on their adventurous journeys and build healthy company cultures that will be able to scale along with the company's success and growth.

To reach that promise, I work with the leaders on their personal development, support the mental health of the team members, and facilitate conversations that need to take place for the company culture to be scalable, intentional and sustainable.

As a teenager, I wanted to become a psychologist. My dad eagerly supported that idea by buying me some books on the subject. The rebellious teen within me decided otherwise and went into computer science. It took me 1.5 decades to get back on track with my passion.

Mindshifting is a cocktail of:
🍹 my tech background that helps speak with analytical leaders their language
🍹 project management education and 6+ years of experience that bring structure into my work
🍹 curiosity that makes me ask lots of questions and dig deep in the conversations
🍹 (apparently) a unique ability to show love and appreciation instead of judgment
🍹 and nerdy interest in human behaviors that help connect the dots of all the above
As a result, you see new perspectives, understand yourself better, and get equipped with the tools that help shift your mind and realign your life.

What my clients have achieved through our work together, in their own words:
🔘 Being the only leader is hard and lonely. It's good to have a person who can listen to me about my struggles, who gets them, and who can support me come out of them without too much of a sacrifice.
🔘 I used to say to myself "I don't have time for this goal". Now I say "I'll find time" - and I find it!
🔘 I started writing down my thoughts. Now nothing slips away in the flow of thoughts.
🔘 My New Year resolution was to get rid of the chaos in the head and life, and it's now achieved - thanks to you.
🔘 I've always wondered whether I am a good father. Now I know that I am. I've done what I could for my kids, and they are good now!
🔘 I was afraid of giving negative feedback out of fear of not being liked. Now I know it's not about me, so I dare to address the issues, significantly improving the work environment in my team.

Entrepreneurship is hard and it's easy to make it a lonely journey. But it doesn't have to be lonely! You can be heard, understood, and supported. 

Want to find better, more sustainable ways to achieve your company and personal goals? Schedule a 90-minute Mindshifting Intensive here: https://annaliebel.as.me/strategycall

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The Battle

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Anna Liebel 🇺🇦

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