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

Having scaled 2 startups the hardest phase is

0 to 1.

It’s lonely. Messy. And very different to scaling.

A few things I wish every first time founder knew early:

- Speed matters more than polish. Perfect is usually just fear in disguise.

- Customers beat opinions. Including your own.
One clear problem is better than five clever ideas.

- Do things that don’t scale. It’s literally the point.

- Momentum is emotional. Protect it aggressively.

- Revenue fixes more problems than strategy sessions ever will.

- Hire later than you think. Fire earlier than you want to.

- Focus is saying no when saying yes feels productive.

- Most things won’t work. That’s not failure. That’s the process.

- Your job is belief. Especially on the days it feels irrational.

0 to 1 isn’t about building a company.
It’s about proving one should exist.

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

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

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.

Having built a 90+ person company where everyone was in the office every day, one thing is clearer to me now than it was back then.

Culture was easier.

Not better because we were smarter. Easier because proximity does a lot of the work for you.

Back then, culture happened by default.
You absorbed it just by turning up.

Now, building teams remotely, I see the trade offs much more clearly.

A few honest reflections:

Culture in an office is ambient. You learn how to behave by watching others. Remote culture has to be explicit or it doesn’t exist.

Momentum used to come from energy in the room. Remote teams need systems to replace that energy, not just good intentions.

Trust used to be built out loud table to table, and lunches. Remotely, it’s built through consistency and follow through.

Feedback used to be casual and constant. Now it has to be intentional or it never lands.

None of this makes remote worse. It just makes it harder to get right.

Remote gives flexibility, focus, and access to great people.

Office gives shared context, speed, and emotional glue.

Different tools. Different costs.
The mistake is pretending the cost isn’t there

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.

Working on a UK Government posting, driving investment between the United Kingdom and North America, based out of Montréal in Canada. Focused on the Space, Technology, and Critical Mineral sectors with a portfolio ranging from micro-satellite manufacturing to rare earth extraction to artificial intelligence infrastructure.

Adaptable and results driven with a blend of start-up experience in rapid-growth environments, and a strong foundation in operational leadership and execution through a decade of military service.

Skilled in cross-cultural communication, fluent in French, with advanced Spanish, and experience of international private-sector businesses, providing a broad understanding of global commerce.

Motorcycled around the world, breaking the record as the youngest person to do so. British - Canadian dual-national.

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