Like many experienced entrepreneurs, I spend a considerable amount of time advising startups and early stage companies. I prefer to catch them at inflection points where my time will be most valuable for them and most rewarding for me. Some examples are the critical early decisions about funding, team members, and product strategy. A dispassionate third party look at such questions can help clarify the next steps to be taken, and it can often ferret out interlinking decisions or disagreements within the founding team.
There’s a balance between calling on me only when there is an urgent need and more routinely keeping me in the loop. The latter avoids frequent retraining on the company mission, helps me understand the sequence of events leading up to the current situation, and enables me to get to know well the players. It keeps everything in context and helps me render more thoughtful advice. The former, exemplified by sporadic office hour visits, results in more“drive-by” opining that may not or may not match the real needs of the moment. But even office hours can be a starting point that eventually leads to a relationship and a more consequential result.
If you have children or grandchildren, you watch them go through all the stages of creating their lives. In the early years there are inflection points nearly every day as physical and behavioral skills are acquired. Adult supervision is mandatory. When a child can easily take care of basic functions and carry on a meaningful conversation with an authority figure, the intervals between inflections grows longer and longer. In the teen years, “self-inflection” is the norm; those kids have had enough of mom and dad supervision and want more freedom of decision making. Don’t worry, they’ll always return as they age, and they’ll be around when they need your financial help for such inflections as making a college choice.
Very early startups are like infants and will soak up everything you provide them in the way of how-to’s and general knowledge. Once they’ve gone through a funding round or two and have a real board to call upon and report to, and they have paying customers and a payee headcount, the advisory channels get more solidified and formalized. Unless I have gotten deeply involved, I’m off to my next batch of eager learners. We all know folks who are too eager to press their opinions on startup leaders and who wear out their welcome. I try to be careful to spend my time when and where I’m sure I’m wanted and where I’m confident I can do some good. That doesn’t keep me from making off-the-wall suggestions drawn from my experience; not a day goes by that I don’t see a new business plan that I have already seen executed by a dozen other entrepreneurs. Founders may pay attention or may ignore me on that point; they always find it hard to swallow that their uniquely charming baby has already been delivered and sent out into the world by others. I realize there are always nuances to every product design and business plan, and that the target markets may support multiple winners, and far be it from me (most of the time) to tell someone to quit their dream and start over. In my next life, perhaps I will start the “Reinvention of the Wheel” fund for those undeterred copycat founders.
Let’s look at a sampling of specific inflection points that have risen to the fore in recent days.
We have just calculated that we do NOT have enough cash runway to complete our MVP and make us attractive to the capital we will need to succeed.
This, unfortunately, is the hardest money to find in more conservative markets like Atlanta. I may be able to suggest some prospective investors who like your space, but, until they have really gotten to know you and have come to respect your skills, they are going to be slow to pull the trigger. All of your mentors and advisors should be asked for introductions, but keep in mind that the investment dollars will have to be attracted by you and the story you sell and won’t flow based on a second-order recommendation. You can’t wind back the clock and delay your start until you have money in hand, so your alternatives are very limited. The downside is having to ice an idea and disperse the founders in hopes all can be reassembled later when some funding magically appears. Don’t hold your breath on that. Your best bet may be to find a customer or vendor whose upside can be dramatically improved by your completion of your work and who has tangible financial motivation to help you get there.
My co-founder is only able to work part-time at less than market wages, and we are falling behind on development.
This is another situation that is hard to fix after the fact. It may be time to have the hard discussion about reeling in those founders shares and finding a replacement. That’s emotionally difficult, but investors are never sensitive to a plea for help to support a recalcitrant player who signed up with full knowledge of the situation and now has become unable to finish the drill. You did install some vesting rules up front, right?
We raised some seed money at such a high valuation that we can’t possibly grow into that before we need our next round.
Even though the business is doing pretty well, your original “conservative” projections were a bit strong. Now, when you run your waterfall chart, you see the corner you’ve painted yourself into. No typical multiple of revenue will equate to the valuation you need to keep the next round marching upward. Perhaps you can try to a bridge note to allow you some catch-up time. If you make that available to all your shareholders pro-rata and allow it to convert at a discount to the next priced round, you may get enough takers for this to work. No shareholder benefits from a down round, which often leads to a spiral of down rounds. Work within your current family of investors to see if they have the capacity and the willingness to do what is best for all. Offer some personal concessions if you can, e.g. delaying vesting, reducing pay, or otherwise sharing the pain.
Our key developer left before we signed a contract with her.
It will be much less expensive to deal with that in the present than let it cast a cloud on your proprietary work in the future. Perhaps a cash payout or some options will do the trick. This is a prime example of all the things you can overlook in the pressure cooker of the startup environment that will come back to haunt you later. Keep everything as clean as possible from day one, and you’ll thank yourself when another party is doing due diligence on you in advance of your big exit payday.
We just got rejected in our bid to present at the conference of most relevance to our attracting investors and/or customers.
It’s a very competitive world in tech startups. You have to be better than your opponents in your chosen specialty, and you also have to be better than companies in adjacent spaces that are chasing the same investors and customers. Evidence of this often comes in denial of a place on the podium where you’d like to be presenting. The best fix for this is better preparation the next time around, including lots of outside coaching and close looks at what others have succeeded in presenting. You might be able to work the edges of a conference by walking the floor, attending the sessions, and inviting prospects for nearby meetings with you, your team, and your pitch. That’s a long shot, but it’s a shot.
We can’t afford the legal fees to get necessary regulatory approvals for our product or service.
Legal fees are a cost of doing business the right way. They are often viewed like a high-priced trip to the dentist’s office, but that too is a necessity for healthy living. Tech law firms that work with startups and early stage clients can be very careful with your billing and generally will try their best to keep you from getting ahead of your skis by not creating documents and doing projects before they are absolutely necessary. And, they sure can keep you out of trouble like the employment issue mentioned two paragraphs above. It’s a heckuva lot less expensive to do proper preventative legal work rather than having to do costly repairs down the road.
My family is ratcheting up the grief about all the hours I spend on this venture and for which I get paid little.
This is the big one. If you have a family, and particularly if you have children, you depend on their support and their belief in your endeavor. It’s not fair to deprive them of the standard of living in their peer group while you chase what may turn out to have been just a dream. The best policy here is transparency. Keep everybody on board by making sure they understand the task and the potential upside. But, keep it honest. Love may be patient and kind, but transparency and honesty are the least you can offer in return. This gets to be a major inflection point if an exit is on the table and there’s the big question of whether it’s better to take some money off the table now or to continue to bat for the home run. The family should get a vote on that decision.
I’ve just given a few examples here. If you think you are at an inflection point, come see me or anyone you trust as an advisor. That’s when an outside look can be most valuable to you.