Top 4 truths as an entrepreneur
Lots of buzz about being an entrepreneur.
Students attend classes, work for start-ups, and begin ventures. There are centers on campuses and “best colleges” or “best MBAs” for entrepreneurship. We need entrepreneurs, this is where creativity and innovation come to the market. We build new things, we distribute hope and opportunity. Awesome. Also, not 100% as much of a party as movies and press like to make it. As an entrepreneur, I have a view of the truths.
As we begin 2025, I enter my 5th year being an entrepreneur. I do not come to this title easily. I’m absolutely an accidental entrepreneur. I did not take these class in my MBA program. I did not set out to to this in my early career. Certainly as a parent with 6th graders and a 25 year career behind me, it might not be the ideal career at this stage. However, it had to be.
Now, with some days behind and plenty ahead, I am taking some time to reflect. This is my way of getting grounded AND fueled up, for the year ahead. By the way, that is my time horizon. One year. Quarter by quarter. Beyond that, the view is foggy and that is too hard to manage.
It brings me very much into the present. To today. Each day, what is important.
Of note, today is Saturday. Yes, I’m working. It is not because I want to or feel I have to. It is because the things I need to get done I’m excited about. Also, on Friday, my family had some needs and today, we have a quite day. They get favorite TV, I do some quality work on some important things and tap my creative energy.
I was also enjoying some coffee, texting a dear friend, and reflecting. I felt the bubble up of some things and thought sharing would be good. For my focus and for all of you.
4 truths as an entrepreneur
Passion
Believers
Criticism
Scarcity
Truth 1 // No one will be more passionate than you.
My personal truth is that I am a very passionate person. I believe deeply in what I do. This extends to our team and our business. It means that our mission is deeply meaningful. It is about others - getting people jobs. Good jobs. I’m mad about the cost of education. I’m mad that there are different layers of education. I am excited about closing equity gaps in employment through educating everyone on how to find a job.
See…that is the passion coming out. I also won’t apologize for it. It is the jet fuel you need to start a business. More importantly, it is essential to sustain you, your team, and your business going forward.
Imagine running marathons week after week, for 3 years. You tell people your idea, they scrunch a face looking uncertain. You speak to a potential investor, they don’t get it or you don’t perfectly tell your story. Boom, like Squid Game, conversation over. (Sorry, the analogy is too good!). A customer says yes, then no, then YES, then delay, then yes! Up down up down up down.
In the end, no one believes in you more than you do. You must believe, it is the armor that allows you to fend off the up downs. To move from the no’s to focus on the yes. To email customer after customer after customer. To ask again and again, just try it. If A won’t work, how about we try B?
Passion can also be the monster within you. Too much can be off-putting to people. People you are selling to, your current customers, potential investors, people on your team, your family, the person at Starbucks you linger to long to show them your app….
Passion can also create gravity. You may not be finding the business model that will enable growth, scale, and making money. It can also be dangerous as signs may be there or feedback given which mandates some adjustment. Conviction may put you in a situation to say, “If I just keep pushing…X will happen…more time, more $$…”
KEY QUESTION
Is your passion still able to help you build a sustainable business? REALLY?
Truth 2 // Find people who believe in you and will scream that on a busy street
Over my career, I have invested in people. Through leading teams, mentoring, advising, and coaching. I became a coach because I wanted to champion people, not judge in hiring and promotion. I now fully proclaim I am a human capitalist.
I apply this in a variety of ways.
When we bring in team members, the first consideration is do you believe. Will you tell others about what we are doing. Our team members are our best sales people. Will you step out of your comfort zone to advocate for our product in your world.
Is this a big ask? Absolutely.
Is it essential? Absolutely.
We are a start-up. World of mouth is essential. If our team members won’t go out and shout about us, how can we expect any customers to love us to. Word of mouth is crucial.
I get this a lot from people. “I think what you are doing is great!” Then I ask, would you speak on our behalf. To the career office? To your friends? To potential investors?
Truth: Many people won’t. Even employees. Even past customers.
Now, I work hard to fine tune my radar - who will do this? I test it early. I will ask an intern, “hey, can you reach out to a group of people, tell them what we are doing, ask for X.” I learn very quickly who believes and who does not.
This is extremely important with early customers. I am fortunate. I will absolutely say, lucky, we have some early customers who are willing to be a voice for us - to other customers and to investors. Just this week, a customer we work with (I hate the term customer - more of a partner), emailed me to ask if we wanted an introduction to a school. ABSOLUTELY!
I have no expectation of this. However, it is strategy. Sales strategy. If we serve each customer/partner well, these individuals become part of our sales force. In a small team, as a start-up, this is crucial. It makes that first “sales” meeting way easier.
What I know is that action here is required:
The entrepreneur must ASK others to act on your behalf. People are busy and don’t always have time to just sit around and think, “How can I help Pam’s business??”
Assess if and who is acting on your behalf, and invest there. Be intentional, fire up your believers.
If others are not acting on your behalf, there is potentially a problem. Could be simple like you are not asking enough. Could be your relationships, maybe they are more take than “give and take.”
Test your believers - next steps
Find/engage:
Assess board and customers
Setup a 30 min meeting
Make a specific, easy ask
Follow-up, assess
Truth 3 // You must expose your product and business to criticism
When we starting building our software product, Archer Job Search, I did a good bit of reading. Hello Start-up was an awesome book, resources from YCombinator, various workshops through the Polsky Center at the University of Chicago, and other relevant blogs.
I made a drawing. Hand scratches.
I created a mock-up, in powerpoint.
We had a firm do a clickable prototype.
We worked with an awesome partner to do a multi-screen design.
At each step, I would put the picture in front of people. Then, I cringed.
I braced myself for what people might say.
Would people poo-poo our application?
Over time, I embraced this more. A pattern emerged. People would say WOW! Then, click through. Then, tell me (or others on our team) what they liked. Then, they would make suggestions.
I also realized that people only filled with criticism might not represent our target market, especially in the early days. This is was feedback and informed our go-to-market plans.
We had a great new client at a large university and launched a pilot in Sep 2021. In Nov, we traveled to campus and met our users - STUDENTS! We went through a questionnaire to collect feedback. It was exceptional. We had “hunches” about our roadmap and some of those were confirmed, some were adjusted.
I have now changed my mindset about this process. It is not criticism, it is feedback. It will make us better. We are working to build a culture in our team and company at this early stage where we listen. Our customer, the job seeker, is the #1 priority. We are trying to fill a gap and one of the challenges is that listening does not happen enough and the right things/needs are not well prioritized.
This is in our DNA.
I have had to change myself here too. I love being an entrepreneur because I like to bring my ideas into the world. I like autonomy. I dislike committee-based approvals. I like to go fast.
I do realize front-and-center, listening is my best strategy.
I have talked with 2 dozen VC and angel investors in the past 3 months. I have refined the story of the business, the pitch, and the focus. This makes us better and stronger.
Be intentional to speak to customers
It is better to hear criticism (aka feedback) and adjust than to have no one buy what you are selling or miss a big opportunity.
Truth 4 // Advice flows freely, money comes scarcely
Now that we are squarely in a launch and scale phase, I dedicate a few hours a week to speaking with 3 groups - 1) Other start-up founders, 2) VCs, and 3) Mentors.
Oh, I’m talking to my team, customers, and potential partners too. But, I’m speaking here about the advice and money side.
Let’s talk money for a second. We are a perfect example of a pre-seed start-up. We have been in market 9 months, have a product, have customers, and have revenue. We have evidence of product-market fit, user feedback, a decent NPS score, and what I think we can confidently say is “traction.”
We are doing a pre-seed raise, seeking about $500K for 2022. Because we have revenue, we can fund the business through our sales and this raise…ideally.
Let’s run through some data:
Contact list - 200 individuals (prior colleagues, clients, referrals)
Outreach - 50 people per week
Meetings - 10 per week (customers, investors, advisors)
Investors - 4 (so far, since October)
My goal is 10 investors in our pre-seed round. That may take 125 meetings.
It also means, 60% of those meetings don’t progress to a YES.
What do they do and why are they valuable?
FEEDBACK // I run through our pitch each time. I fine tune. I listen.
IDEAS // To help our product, to focus our business development
INSIGHTS // I ask questions and get insights from experience, then, I can apply.
SALES // I just might get someone who wants to buy our product!
Here is the big thing to know. This is NOT easy. I spoke to someone on Friday, they gave me time, they gave me advice. This individual kept saying, “I’m not sure I’m helping.” Truth - this person invests, has a network, knows what founders need. There is a holdback. Advice costs nothing to give. More action is expensive to give.
I find it frustrating frankly. Now however, after some time, I have come to accept it.
There is a “game” in the world of start-ups. At times, I now refer to this as The Start-up Squid Game.
Every conversation is:
Red Light/Green Light.
I’m not aiming here to be rude, graphic, or pessimistic. I am speaking truth, my truth.
I’m willing to take on these challenges because of the passion, the mission. I spoke about this above.
At a certain point, you have to convert the game to the Snowball Roll. One success or positive outcome leads to another, and another, another, another. Your momentum grows like a snowball, rolling in the yard.
I am looking to roll more snowballs. I will always have these conversations, gather advice, take meetings - you never know the potential opportunity. This however needs to be a portfolio allocation decision. My time is the portfolio. I need to allocate the right amount to advice getting. More and more, it is more heavily invested in money getting - this means, business development and potential investors. Of that, more is for business development.
As an entrepreneur, I now understand that my time allocation is crucial. For me, the founder and the members of my team.
Check your time allocation
Are you balanced? Are you investing in the right things? Time is your scarce resource, value it accordingly!
Does this resonate, I’d love to hear from you. Any challenges you are facing?
For the record, I don’t think these truths apply only to entrepreneurs. They can be extrapolated to any professional. Same for job seekers. Job seeking is just another form of selling a product/getting investors. Your buyer/investor is an employer!
Good luck, Whatever you are doing or challenges you face, it is not you alone. We are all there or been there.
EdTech founder
Human Capitalist
CEOmom