Entrepreneur Conversations
Most of what founders wish they had known was knowable at the time
Ask an owner what they would tell themselves before they started and the answer is rarely a secret. It is usually something ordinary that nobody mentioned or that they did not want to hear. In this conversation an owner goes through what they did not know about money, time, customers, people and themselves, and the room can ask anything it likes.
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People who are about to start a business mostly hear from the ones who succeeded, and mostly hear the finished story.
A founder asked what they wish they had known is often the first person to say it aloud in years. It is a different question from 'how did you do it', which invites a tidy answer. This one invites the untidy parts: what was underestimated, what was ignored and what was learned only by paying for it.
Hearing the same answers from several owners helps a listener see what is common and what is particular to one business. A single speaker cannot do that, but a single speaker can still give a room a list of questions it did not know it had.
The conversation does not tell anyone whether to start. It is for people thinking about it, people in the first year and people who started some time ago and want to compare notes honestly.
What the speaker is briefed to cover
35 topics across 7 areas. Seven things an owner is likely to say they would tell themselves.
About MoneyKept to the experience, with no figures.5
- How long it took before the business paid them anything
- What they lived on in the meantime, in general terms
- What they spent on that did not matter
- What they should have spent on and did not
- How they kept personal and business money apart, or failed to
Speakers do not give financial advice or recommend any product. They describe their own experience.
About TimeHow the days really went.5
- How the hours compared with what they expected
- Which tasks took the day without feeling like work
- What they gave up, and for how long
- How they learned to say no to something
- Whether they would plan the first year differently
About CustomersWho they are, and who they are not.5
- What they assumed about customers that turned out to be wrong
- Who the first customers really were
- What customers asked for that was not in the plan
- What took longer than expected: finding, convincing or keeping them
- What they would ask customers sooner
About PeoplePartners, family, staff and the people who helped.5
- What it was like working with a partner or relative, if they did
- How they found the first helper or employee
- Who they wish they had asked for advice earlier
- Who gave good advice that they did not take
- What they would say to the family at the start
About the Work They Did Not ExpectThe unglamorous parts.5
- Paperwork, registrations and records they did not know about, in general terms
- Chasing payment, handling complaints, keeping accounts
- Tasks they had to learn from nothing
- Which tasks they handed over, and when they wished they had sooner
- What nobody mentioned that took more time than the product itself
Where rules come up, the speaker says they are describing their own case and tells the room to confirm the current position with a professional.
About ThemselvesThe least discussed part.5
- How they behaved under pressure, and how it surprised them
- When they doubted it, and what they did
- Habits that helped, such as keeping records, resting or asking
- Habits that hurt
- Whether they would start again, in the same way
What They Would Tell Somebody Starting This MonthSaid in a few sentences.5
Speakers are asked to say that their list belongs to their own business and time, and that a different business may need a different list.
- Three things they would say first
- One thing they would say not to worry about
- One thing they would say not to put off
- What they would ask the person before offering any advice
- What they hope the person does not take from their story
What the speaker prepares
- A short, ordered list of what they did not know, with one example for each
- At least one piece of advice they were given and ignored
- What they would tell a younger version of themselves
- A willingness to say what they still find hard
What the room can ask
- What did you underestimate most?
- What was the first thing that surprised you?
- What would you do differently with the first year?
- Who should I talk to before I start?
- What is easier than people think?
- Was there a day you wanted to stop?
How the conversation runs
The speaker goes through what they wish they had known for about fifteen minutes, from a few notes, and a facilitator then takes questions from the room, written in advance or asked on the day. Before the session the speaker is briefed on not promoting their business, not giving financial or legal advice, and saying clearly that theirs is one path. The host chooses and invites the speaker and agrees the length and the audience with us.
What your students leave with
- A plain list, from one owner, of what they did not know at the start
- Questions to ask a founder before starting something of your own
- A better sense of the difference between what is hard and what is only unfamiliar
- A view of how money, time and family are affected in the first years
- A sense of which advice the owner got and ignored, and why
- A speaker to ask further questions, in the room or afterwards
Scheduled sessions
Nothing scheduled yet
Sessions are arranged with a college once a date is agreed. Ask us and we will find the right person for it.
A student rather than a college? See what is coming up, or ask your placement team to host this.
Ask a founder what they would tell themselves, before you start.
Tell us who your students are and what stage they are at. Sessions are free for participants.