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

Big news at team trumpet 🎺as we finally say what all our customers already know and move into our next era.

We are way more than just a digital sales room. It's a feature now, not the product.

While our DSR remains #1 globally and will continue to be so, we felt it was time to create a new category.

🎺 Rory Sadler explains it best in the short video....

Over the last 40 years we have seen sales tech change from CRM to Sales Enablement to Rev Enablement to Rev Intelligence and we now have a tonne of siloed products...

Trumpet's next chapter aims to combine all of these into one AI-powered workspace where Enablement, Collaboration and Intelligence all work together.

We are the Intelligent Go-To-Market Layer for Revenue Teams 

...combining CMS, Sales Rooms, Workspaces, Collaboration (internal and external), Org Charts, Proposals/Quotes, Buyer Engagement Intelligence, Actionable Intelligence, Coaching, 10+ other AI features plus 55+ integrations....

One connected, collaborative and intelligent tool.

Over to you Rory....👇

Co-Founder trumpet 🎺 | Founder DesignMyNight (Acquired '19) 🍹 | Investor in 55+ Startups 🤑 🏳️‍🌈

Being a second time founder is wild.
You are still guessing, but you know exactly which guesses nearly killed you last time.

With DesignMyNight I learned plenty the hard way.
This time round with trumpet 🎺 I have been very deliberate about changing some of my defaults.

Here are the 5 biggest changes I have made.

1) I designed the business model before the product

First time I was obsessed with the product idea. The model was an afterthought. Now I start with ACV, margin, sales cycle, who actually pays and how often. If the numbers did not work on a simple spreadsheet, I do not build it.

2) I am ruthless on people quality, not people quantity

First time I hired for relief. Too busy, drowning, just get someone in.
Now we hire very slowly with scary high bars. One great operator beats three people we need to manage every day. 

3) We optimised for distribution from day one

Before, product was the obsession and distribution was an afterthought.
We built, then hoped. Now we only build things I already know how to sell. Audience, channels, partnerships, content. If I could not see the path to customers, we did not build it

4) I was far more intentional with investors

First time I was just happy anyone said yes. Wrong. This time we reference checked investors harder than they reference checked us. Values, speed, how they behave when things dip etc. Money is a commodity, behaviour is not.

5) We run the company on a clear operating rhythm

Last time it was vibes and firefighting. Some weeks we were busy but not actually moving. Now we have monthly metrics, clear priorities, operating playbooks and clear owners for each area. t is a lot harder for the business to drift without anyone noticing.

Second chances are rare.

The trick is always be learning and not wasting the pain from the first

At trumpet 🎺 we recently told a big paying customer no.
To a chunky custom build that would have made us hit Q1 quota already.

On the surface it looked perfect
Huge logo
Excited champion
Budget approved

But here is what actually went on behind the scenes as there are learnings for all I think...

- The request would have dragged us off our ICP
- The use case was cool but miles away from our core users
- It would have pushed trumpet toward being an agency not SaaS
- The feature did not compound
- No clear path to reuse across our base
- No way it made the core product better for everyone

Sales loved it for the wrong reason
 
It made the deal bigger
But it would have slowed us down

❌ High implementation cost
❌ High support cost
❌ Low reusability
 
So we told them no
Respectfully
Explained why
Offered a trimmed version that kept us closer to our main product and kept them happy

We did lose some short term revenue

But we kept something more important

A product that gets better for most of our customers and keeps us bang-on focus across the board

From the outside it is easy to assume growth comes from every yes

At our stage it can also come from choosing the right no.

We just crossed 1000 reviews on G2. F**k yeh! 🥳
And we are still sitting at number 1 in our category globally

I am proud of that
But I'm even prouder of how we got there

Every single review is treated like a product slack message from our team
• The glowing ones show us what not to break
• The brutal ones show us what to fix next
• The detailed ones end up as product specs

We read them ALL
We tag them
We turn them into roadmap decisions and UX changes

This is not a vanity metric for us
It is a feedback engine

So THANK YOU to every customer who took time out of a very busy day to write one line or ten paragraphs about us

You helped us get to 1000 reviews
You will be the reason we earn the next 1000

Relentlessly customer centric is not a tagline for us
It is one of our trumpet values and we stick to it religiously.

Having observed over 50 founders that I've invested in. Here is a list of 50 characteristics I think make a good founder:

1) Obsession with the problem
2) Ability to hear no ten times and not take it personally.
3) Writing things down clearly
4) Knowing when a tiny ugly experiment is better than a beautiful strategy
5) Hiring people because they are better than you
6) Firing fast when your gut has already decided
7) Saying I do not know without flinching.
8) Caring more about cash in the bank
9) Being honest in investor meetings
10) Being able to sell
11) Protecting deep work time
12) Admitting when the market does not care about your idea
13) Treating customer complaints as free consulting
14) Knowing the difference between a bad week and a broken business.
15) Letting your team ship work that is not perfect
16) Making clear quick decisions in meetings
17) Staying calm when numbers are bad
18) Being able to explain what you do to a kid or parents
19) Choosing boring consistent progress over heroic all nighters
20) Talking about money openly
21) Saying no to cool opportunities that do not move the core metric
22) Giving credit to the team in public and feedback in private.
23) Knowing when your own ego is the real blocker
24) Treating investors like partners not parents.
25) Keeping your personal burn rate low
26) Asking your best people what they really want and actually listening
27) Being willing to walk away from mis-aligned money
28) Staying curious about competitors instead of obsessed
29) Realising culture is set by your actions not what you simply write down
30) Checking the numbers yourself
31) Becoming less important to daily operations as the company grows
32) Being honest when someone great has simply outgrown the roles you have
33) Keeping a small circle of people who will tell you when you are being an idiot
34) Turning complex plans into one simple next moves
35) Not confusing being busy with making progress
36) Knowing which metrics actually matter at your stage
37) Staying kind when you are stressed
38) Being able to pitch with the same energy at all times
39) Choosing long term trust over short term wins in every deal
40) Protecting your sleep
41) Not needing to pretend things are amazing when they are not
42) Giving your team context instead of random orders
43) Letting go of old decisions when new information arrives
44) Knowing when you are not running toward a clear goal
45) Saying I messed that up so the team feels safe to own their mistakes too
46) Caring about the lives your team beyond their output
47) Choosing a simple product/feature that actually ships
48) Being willing to be misunderstood for a while when you take a non obvious bet
49) Designing your work around your energy
50) Wanting the company to win more than you want to be the hero of the story

Which do you nail? 
Which could you improve on? 
What's missing?

Planning a year as a founder is not about a big strategy offsite and a shiny Notion page.

It is about a few hard decisions you are willing to live with for twelve months.

Here is how I now plan my year.

1) Start with the uncomfortable question - What has to be true in twelve months for this year to have been a success?
- Revenue
- Team
- Product
- Your own life

Write the answers in one sentence each. If it does not fit in one sentence you aren't getting to the core

2) Pick 3-5 non negotiable company priorities/themes

Not ten. 
Every project must map to one of the three. If it does not, it dies.
This is how you protect your team from chaos and yourself from distraction.

3) Turn priorities into bets not tasks
Instead of writing "Launch new pricing"
Write "Double expansion revenue by testing three pricing models by June"

Good bets have a clear outcome, a deadline, an owner, and a maximum spend.

4) Build a stop doing list
- Which customers will you stop serving
- Which features will you stop maintaining
- Which meetings will you cancel

Good strategy is also choosing what you will ignore.

5) Decide your personal rules up front
- Maximum hours you want to work
- Non negotiable time with family or health
- What you will say no to even if your ego wants to say yes

If you burn out the plan does not matter.

Your strategy is not what you write in January
It is what you refuse to compromise on in November

Having exited a company after a decade building, there is something about the exit planning I wish I was told earlier.

Your real exit plan is not a number
It is your life

We obsess over valuation, equity, secondaries etc but it hides a simple question - What do you actually want your life to look like before and after any exit?

For a long time my own plan was basically...
Work as hard as possible
Build something big
Sell
Life will somehow sort itself out

We design all aspects of our business and products in detail but treat our own life like an afterthought slide at the end of the deck

What did I want after an exit? What did I want my life to actually look like? What would I need to make this happen?

The shift for me was treating life design as seriously as a startup strategy
Very practical things

- Energy map
 When in the day do you feel good
 Do you want long deep work blocks or variety
 Could your role reflect that

- Relationship map
 Who are the people that truly matter
 Who gives you energy and doesn't drain it
 With who do I get genuine enjoyment with
 Who do I learn from

- Work map
 What parts of the game do you still love
 Selling, coaching, product, content
 Can your next chapter be mostly that, instead of owning everything again

- Money map
 What does enough actually mean for you
 Not for the tech press
 For you
 What would financial freedom look like?
 If you wrote that number down, you would probably act differently

Life design is not a fluffy vision board
It is a set of constraints you choose on purpose

If you're lucky enough to be ready to build for a second time, make sure you stop and think what you REALLY want out of it this time around.

You get plenty shots at building companies but only one shot at life 🤷

Building a startup is loud
But what if you're an introverted founder?

I am not the loudest person in the room
Never have been

For a while I thought that meant I was not the type of personality to be a founder

So I did what most introvert leaning founders do
Forced the big energy
Over prepared every social situation
Came home absolutely wiped

Over time I realised I did not need to become more extrovert

I needed to design the company around how I actually work best

Here is what that looked like in practice:

- One to one as the default
 Big networking events or founder events drain me
 So I stopped going 
 I would message people 1 on 1
 Have one good conversation
 Fewer people
 Better relationships
 More deals
 Less acting

- Writing as a superpower
 Extroverts often win in the room
 Introverts often win in the follow up
 I leaned hard into clear written updates for investors
 Thoughtful emails to partners
 Long form documents for the team instead of endless meetings
 It gave me time to think
 And it made decision making cleaner

- Designing my calendar like a battery
 Back to back calls all day
 No chance
 I started blocking recovery time after anything high stimulus
 No other meetings straight after
 Even thirty minutes to reset made me far better in the next conversation
 Leaned into async collaboration - emails and looms instead of meetings

- Hiring my social opposite
 Instead of worrying that I was not the big energy founder
 I hired people who were
 Commercial leaders who loved being out there
 Co-founders who enjoyed the spotlight
 Team leads who could shine without needing me all the time
 Their natural state was my unnatural state
 The mix worked


None of this means introverts get a free pass on the hard stuff

You still need to sell
You still need to pitch
You still need to have tough conversations

The difference is you can choose the format and the rhythm that suits you instead of copying the loudest founder you know

Some of the best companies I have seen were built by founders who do not dominate the room

They listen longer
They think deeper
They pick their moments

You do not have to change your personality to build a big company

You just have to stop building a company that constantly fights it.

Having grown two startups myself and backed a tonne more founders. 
The money trap is a real problem not many talk about.

As revenue grows, funding rounds grow and more money is in the company bank, the money fears do not disappear they often get louder

For most founders it sounds like this:

- Fear of going back to zero
 So you cling to every client
 You keep bad revenue
 You avoid bold bets
 Safety first slowly kills the upside

- Fear of being the one who ruins it for everyone
 Team
 Family
 Investors
 So every decision carries a silent courtroom in your head
 You delay hard calls because you are scared of f'ing it up

- Fear of lifestyle creep
 You upgrade your life faster than your company can justify
 Now you are building just to stand still
 Every month feels like a test you can fail
 A taste of what you can have one day but you're still not there yet

- Fear of stopping
 Money became the scoreboard
 If you slow down you lose your identity
 So you keep raising
 Keep building
 Even when the game you are playing no longer feels like yours

None of these fears are solved by another funding round or a higher valuation

They are solved when you decide what enough really looks like for you.

And build from there.

And the band keeps growing 🎺

Following stronggggg recent growth in the States, we’re building trumpet’s Customer Success presence een further and looking for someone who wants real ownership from day one.

You’ll own your own book of customers end to end.
Onboarding. Adoption. Renewals. Expansion. Advocacy.

You’ll work closely with Russell Mitchell - Head of Customer Success, Alison Prator - Founding US CSM and the wider GTM team to help customers get real, measurable outcomes from trumpet and to help us build the CS playbooks we’ll scale with.

You’ll love this role if you:

• Care deeply about customer outcomes, not just activity
• Enjoy commercial conversations and helping customers grow
• Want to help establish a startup’s presence in the US
• Thrive in fast-moving, high-ownership, chaotic environments

This is not a feet-up on the desk role answering support questions that come in! If you want the easy-life this job isn't for you.

If you want real influence over how we serve customers, how we retain and expand accounts, and what Customer Success looks at trumpet as we scale, then this is for you.

If that sounds like you apply here 👉 https://lnkd.in/eim5uFBS

Various Startups

Investor in, and advisor to, several exciting startups: Pave, WithClutch, Default, HappyRobot, Integral, Basis, Gain, DittoWords, Trumpet, Subskribe, NeoSync, Meez, Middleware.io, Concourse, Nucleus, Klu, Glimpse, Storia, and others

Investor & Advisor

Default

Strategic Advisor

Pave

Founding advisor and thought partner to the CEO.

Craft Ventures

Scout

trumpet 🎺

Subskribe

Operating advisor and thought partner to the founding team.

Asana

Channel Partnerships NAMER

Segment

Head of Channel Partnerships

Alto Pharmacy

Alto is the leading disrupter of the $450B U.S. pharmacy space, offering free same-day delivery of prescription medications and patient delight—all powered by technology.

WalkSource

WalkSource saves hotel and airline operators time and money by providing instant accommodation in the event of an emergency, such as a hotel overbooking or flight cancelation. WalkSource serves hundreds of hotels around the Bay Area and is funded by Y Combinator.

Co-Founder & CEO

Co-Founder and former COO @Alto. Incubator and advisor of high-growth startups.
@Pave @Subskribe @Nucleus

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