Early in their careers, it's natural for young entrepreneurs to get much of their advice from a supportive cast of professional allies, mentors, colleagues, and other friends of the cause.
But when the time comes to raise money, this won't be enough. If you want to be able to speak cogently to investors and successfully pitch your story with impactful results, you'll need to understand certain fundraising fundamentals that can come only from the experts who deal with them every day.
When it comes to such guidance, you'll need to reach for the premium stuff. I'm talking the kind of pricey, blue-label consultation poured by the true masters--the elite professionals and specialists sitting at the very top of the corporate food chain.
And the most efficient and indelible way to learn from these giants? Take them to lunch. Do not go to their office. That's a trap where you'll get a half-distracted hour of the pedantic wisdom of the day and be sent on your way with a sound paddling of apathy. By sharing a meal at their favorite spot, you'll be able to pay for a full hour of their time, preferably a cocktail or two, and achieve the kind of candid, camaraderie-laced conversation that's often impossible in a corner office--all around the very specific list of things you need to know.
And who are these high-priced members of the business elite with whom you should be breaking bread (and possibly bank)? There are four of them:
1. The accountant.
America's business schools are the best in the world, but they don't spend nearly enough time on a bedrock business fundamental: how to speak accounting. You may be the second coming of Lee Iacocca in a room, but if you can't easily digest the key financial and investment documents underlying every meaningful company in existence, you're going to get buried.
How do you avoid this? You can help yourself a lot with a lunch invitation to a top-level Big 4 accountant at the power grill of their choice. While plying them with food and drink over the course of an hour, spend 15 minutes going over each of these four documents: a balance sheet, an income statement, a statement of cash flow, and a pro forma. These are the four accounting documents every entrepreneur needs to be able to skim as effortlessly and confidently as the menu at their favorite restaurant.
If you don't know how these documents are different and exactly which line and column to zero in on inside of each, you simply aren't ready to run a company. Everybody who invests in young companies for a living knows how to read these documents, and when a founder or CEO doesn't, it shows.
2. The lawyer.
If you're lucky, the path for your new business will eventually lead you to a negotiating table where you'll sit across from a group of very smart investors looking to make yours their latest portfolio company.
But you'll be ready because beforehand you bought a salad/hanger steak/rich, meaty Bolognese for a power lawyer with a deep understanding of investor rights agreements. And as surely as they opted for the premium sparkling water, they're going to drill into your head the dozen or so traditional protective provisions you need to understand to navigate a VC session. Pre- versus post-money valuations. How common versus preferred stock works. What liquidation preference means. What standard protective provisions are. What pro rata, drag-along, and tag-along rights are. How an option works versus an RSU.
If you don't have a firm grasp of what these terms are, it's time to book some bar time with your friendly neighborhood investment attorney for a down-and-dirty knowledge session that can at least get you around third base in any investor negotiation.
3. The investor.
Once you're conversational in transactional legalese and can thumb through complicated financial documents like the sections of a USA Today, it's time to field test your knowledge with an actual investor. And as a bonus, you won't even need to pay for their time, as meeting ambitious entrepreneurs like you is in their job description.
What you're looking for here is essentially practice, so this should ideally be a VC you don't want money from. But, of course, if they happen to take the bait based on the chum you're throwing in the water, then your first two lunches already paid for themselves many times over. At any rate, your goal should be to see if you're able to have a better conversation with a member of the investor class now that you've done a bit of homework.
It's also a prime opportunity to get next-level around some of the topics of your business that are important to investors--and maybe even informally kick the scuttlebutt machine into action in the right circles on the prospect of your next funding round.
4. The human resources professional.
After what might qualify as three down-the-middle lunch dates any founder might think to take, a meeting with an HR pro may seem like a bit of a curveball. But when your high-level training is in hand and the countdown begins for your company's launch, the time will be nigh for a final briefing about the reality awaiting you after takeoff. Because stuff gets real on the other side.
For example, it's pretty important for any founder to understand that every dollar they pay an employee involves paying 15 cents to third parties. And that's before we even talk about employment taxes, payroll tax, medical insurance, setting up a fair equity program, and more.
But even more important than that is getting a full download on the legal requirements and daily commitments of what a modern cultural compliance program looks like. It may not be the kind of thing you were thinking of when you came up with the idea for your business, but you'll quickly find that taking care of your people is Job No. 1 for any founder. And getting a primer on the many facets involved in this effort from an experienced human resources expert is among the most important lunches you'll ever take.