Investing as a founder vs. via convertible note?

dann harriss Student at Stanford University

April 21st, 2016

Here's a scenario: 3 founders have started a company with, initially, equal equity split between the three of them. Things are moving forward nicely but more cash is needed so it's time to take some Angel funding via convertible notes. However, two of the founders also want to put more $$$ into the company - the 3rd founder can't afford to do so. 3rd founder doesn't really want to be diluted relative to the other two so he suggests that they put their additional money in as convertible notes under the same terms as any Angel investor.

Any comments on this scenario? Does it make sense for founders to put money in as convertible notes? How will that be seen by future investors when there's a valuation round?

Orion Parrott Founder and CEO, Lendsnap YC S16. We're hiring!

April 21st, 2016

I personally recommend the convertible note scenario. It makes it easier to separate the cash vs (apparently) fair equity split. The convertible note will dilute the 3rd founder eventually if it converts, but fair is fair. There are also tax and balance sheet implications to each scenario. My belief is investors look more favorably on the convertible note (as opposed to a non-convertible simple loan) because it won't generally be paid back upon raising funds(depends on terms), which would reduce operating capital available to the business. One modification would be for the founders to put their cash in as SAFEs which are not debt on the company books at all. Outstanding convertible notes don't add much complexity, particularly when the note holders are already on the cap table; they're just more paid in capital, subject to the same calculation as other investor money.

If the founders don't get a SAFE or note for their cash contributions, then what is the alternative? Somehow arbitrarily assigning a fair value to the cash contribution in terms of % ownership of the company. That would be forcing (implying) a valuation on the startup at the earliest stages. Early valuation is not just complicated but subject to significant error in any case. The SAFE or note solves this problem for the founders.

Another reason investors might look more favorably on the convertible note instead of a plain note is it signals commitment and investment in the business. Shouldn't the entrepreneur be long on their own startup instead of playing it safe and earning 0% or nominal interest? True, there is no right answer, it still depends on the particular circumstances. Some people would say the founder should not also put their own money in (or not much) because the external validation of raising funding is another positive signal. Founder investment can help start that tide.

Michael Brill Technology startup exec focused on AI-driven products

April 22nd, 2016

I'd stay away from the convertible approach as it now creates different motivations for the founders - especially if things get tough (and they typically do). The 2 investors may make decisions more motivated to benefit the Series A shareholders while investor 3 will always be more focused on the outcome for common. Even if this doesn't really manifest in decisions, it'll be in everyone's minds and be a source of conflict at exactly the time when the 3 of them need to work together.

Also, it's a slight exaggeration, but a convertible note essentially means 2 founders are just *giving* the company money in most scenarios. It's not likely a large amount of money and it'll convert to a very small amount shares relative to their founders' shares. Yes, there's a liquidation sweet spot (e.g., <= 1X Series A size) where founders would get some of their money back, but statistically it's not likely. Kind of a crap deal for the 2.

A straight note at least has some potential of being paid back... and investors may not grimace if it's negotiated to be paid back at some future time when cash flow allows... or it could simply be negotiated into converting at Series A. In any case, this provides founders most flexibility and doesn't instantly create two tiers of founders.

Depending upon amount of money, another possibility is to improve optics by having the employees paying for some of the expenses directly and then simply file expense forms... it'll now sit on the balance sheet as a payable, not as debt. Psychologically, investors are less fussed about paying back bills than they are paying off debt.

I guess a final approach would that the three amigos all do the same thing (whatever it is) but have the company lend amigo 3 the money.

Joseph Wang Chief Science Officer at Bitquant Research Laboratories

April 21st, 2016

For small companies, it's always about personality and relationships more than money.

Martin Omansky Independent Venture Capital & Private Equity Professional

April 23rd, 2016

Investors will elect to live with any result, or they will pass. You have little control. Also your founder can't avoid dilution. Something about the law. There are ways to handle this, however, but he and you can't a kid consequences. I suggest you talk to a tax attorney a out this matter. Sent from my iPhone

David Jeske Software Entrepreneur, Architect, Manager

April 26th, 2016

A notable issue which I don't see discussed in existing answers is the percentage of the round the 2 founders are allowed to take. Personally, I wouldn't have them take more than 30%, nor should they (individually or collectively) be the largest investor. Doing either of these things can make negotiations with other investors awkward.

Investors at times benefit from safety in a group, by considering the other investors part of their ongoing investment support for the company. However, if two of the founders are the largest investors, it removes some element of outside validation. Investors can't expect to get a frank external perspective from an investor-founder. It also creates conflict of interest, which can be extremely difficult if there is a need to have a down-round in the future.

Keeping the founder-investment percentage low also solves issues with dilution vs the third founder, as 25% of the angel round shouldn't represent enough voting stock to change a voting outcome of "three initially equal founders". It will take an agreement of two founders to make a voting decision, and that's true whether it's 33/33/33 or 38/38/23.

Suryanarayanan A Head, Incubator consulting services at Bhiveworkspace

April 26th, 2016

Another option is optional convertible note. This gives the 2 founders to convert it into equity at their option at a certain discount to the next round of funding and till then a fixed interest accumulates. They can also opt for refund of debt and interest if the next investors agree.

Len Chermack Software Executive in Cloud, Iot, Enterprise & SMB. Proven in Turnaround and Growth in Sales and Services

April 26th, 2016

This is difficult to answer without knowing the effect on the partner who cannot contribute cash. What value does this partner bring that the two with cash are unwilling to perhaps take a greater risk and therefore greater percentage of the company? You see, if these two partners put money in via a convertible note they already have greater ownership at time of conversion. So why have them jump through hoops? Have them put the money in as a loan and set appropriate terms. Perhaps they should receive a preferred note.

In any case internal money is better than outside money for better control at this stage. But if you need the outside angel too, all the better. That person is less attached and therefore if interested there is some validation on the belief you three are on to something.

Neil Gordon Board Member, Corporate Finance Advisor and Strategy Consultant

April 26th, 2016

As others have suggested, interested investors will negotiate a structure that works for them, including restructuring what's already in place. The significant issue is that with two of three founders adding capital to the mix, interests are no longer aligned, a situation that needs to be understood and dealt with.

That the third founder doesn't want to be diluted, despite the other two taking on significant new risk, is a clear warning sign; deal with this now or it will haunt you later.

Wendy Robertson Innovation Strategy and Customer Development

April 26th, 2016

What emerges in an equal partnership is often that it is not equal. It is painful and disturbing to those whose "value contribution" is not expressed in directly attributable revenue or cash contributions. The more strident among us lay claim to this directly attributable value creation. If the intent of the partnership was equal parts value contribution; all originally credentials, skills based, then (as long as the contributions are being made and still relevant) it should be maintained with options being issued to the third impecunious partner at the same price. If there is disparity in contributions in kind or in cash, then best to get it out on the table now. The 'money' will always dilute the others. It doesn't matter whose money it is.

Benjamin Bayat Investor, Illuminate Ventures

April 26th, 2016

The other two founders should invest through the convertible note, same terms as angels.

Investing as a founder vs. via convertible note?

Mastering the Fundraising Game