A constant battle

For starters, valuations of a startup do not change linearly over time. Simply because it was twelve months since raising a series A round does not mean that it will be easier to raise more money or be ready for a step-up in valuation. To reach an increase in valuation, a company must achieve certain key milestones that are relevant to showing progress to market and in most investors eye's progress towards monetization.

It is important to understand what potential investors think is worthy of a step up, but generally valuation is pretty flat in between inflection points where key milestones are reached that earn a big increase.

Active vs. passive investment pursuits

Given that it often takes six to nine months and two-thirds of a CEO's time during a major round of fundraising, optimally you should align progress points into major milestones where efforts can be concentrated for fundraising success approaching the inflection points. That does not mean that the CEO can ignore fundraising in between those major milestones, but should think about waves of active and passive fundraising activities.

Active fundraising is obvious, which is the typical efforts to craft a pitch, meet with investors, nurture investor prospects into lead and following investor types. Most of the effort should be put into the early investors that will lead the round as the first checks are always the hardest.

From my experience rounds develop their own momentum when reaching about 40 percent of their target and even more when reaching 60 percent as long as the prospective investor pool is large enough. However, the CEO cannot ignore the company's progress while the raise is actively underway, as they will typically meet with prospective investors multiple times who will want to hear about progress each time.

Passive fundraising is less obvious, which happens in the gaps in between active fundraising where one round closes and before the next round starts. The primary passive activity is general investor networking, where the CEO should be out expanding their network, meeting new prospects and trying to identify the mostly likely early investors or best fit for the company.

I'm not suggesting this is really a passive activity, as it takes a lot of work. But this should be an ongoing between rounds. This passive effort gives the CEO a chance to put most of their emphasis on the progress of the company to the next milestones, but avoids a cold start to the next fundraising round.

Regardless, there are two best practices in this passive mode. First, use networking techniques to identify good prospective investors for your company and two to work on getting referrals to investors well before an actual fundraising round is open. Getting a referral is obviously to your advantage, because it takes you out of cold-calling mode that has a low success rate.

Meeting an investor while you are not fundraising takes the pressure off both the CEO and investor and gives them a chance to get to know each other personally. Again, many will not be your round leaders or champions to other investors, but this lower pressure effort gives investors a chance to listen and reach out to potential experts in their networks to validate the problem and your solution.

With the relationship established and your solution validation received, moving to an active discussion about investment comes more naturally as well as targeting of the best lead investor candidates leading to due diligence, negotiation and closing the funds.