As a former startup founder, I was often unsure about best practice for proactively communicating with investors ahead of my next round.
Now sitting on the other side of the table as an investor, I wanted to share my thoughts.
Here are five tips I recommend for early stage founders gearing up for their next fundraising round within the next 3-18 months.
Tip #1: Allocate time and speak with *almost* everyone, at least once
The challenge for many founders is that there’s so many demands on your time. As with all things important, you’ll need to schedule and batch time if you want it done – else the urgent always barrels over the important but not urgent tasks.
I’d recommend you carve out a morning or afternoon every 1-2 weeks, but ideally no less frequently than once a month. Batch all of your investor calls in that time, in 30 minute slots. If you want a breather between calls, go Google meeting style and set up 25 minute meetings. Don’t book anything else during this time.
I’d also carve out a bit of this block for proactive outreach yourself. Make a short list of the top investors you’d like to get to know, and get warm intros to them. You should also ask your existing investors who they recommend you speak with for your next round, and ask for intros.
I’d recommend you start by taking a 25 minute intro call with *almost* anyone who reaches out. I say *almost* anyone because you’ll want to take a few minutes to read their website, make sure their overall fund approach matches your company’s strategy, you like their portfolio companies, and you’re engaging with a partner.
Tip #2. Create a priority list and proactively keep in touch with a few
Once you have that, keep a running list, in high/medium/low priority order, of who you like best and for the top few, set up regular calls every few weeks or months. Bonus if you’re organized enough to schedule proactively ahead of time, rather than having the investor do that.
Like a job interview, every interaction is one more data point for both of you. You want investors who are organized and reliable; they want the same from founders they invest in.
In making this list, pay attention to how you feel and your energy level after you speak with an investor. Of course you’ll want to add those that bring you to life, help shed guidance and insights and provide intros that are truly helpful.
However, I’d also counsel you to keep in touch and work with investors who ask tough questions, don’t just nod their head in agreement, and also leave you with direct and often challenging feedback that pushes your thinking.
That approach doesn’t necessarily feel good – but it will help move you closer in the direction of success than cheerleading will. Overall, you’ll want to have a range of investors as partners and board members over time, operating as a brain trust.
Tip #3. Regularly send investor and advisor updates
Once you’ve developed a list of supporters, the million dollar question is how to manage your growing tribe without letting this take over your entire schedule.
The answer: manage the long-tail with an email list or video update.
Choose a cadence that feels achievable. Monthly is great. I wouldn’t recommend more than bi-weekly, and quarterly is the longest you’d want to go without an update.
I recommend sharing what’s top of mind for you, biggest wins and highlights for your business, some challenges and roadblocks, shoutouts to investors and advisors who have provided assistance, and also requests for help (see the next tip).
Make it informal and conversational. Write the way you talk. If you’re struggling to do that, you might consider recording your update out loud, and then transcribing it.
As with all great writing, the more concise you can be – by focusing on the few things that matter most – the more impactful it will be.
Tip #4. Ask for help and see who steps up
As part of your updates, make sure to include clear and direct asks for help.
These might include key hires, investor intros, feedback on different parts of your business, requests for deep-dive sessions (like goal setting/OKRs/key metrics, sales strategy, capacity planning, financials, product or engineering planning, etc.).
Then watch to see who follows up and helps. Just because an investor doesn’t follow up, it isn’t necessarily a negative sign — but hearing back and getting help from investors on your priority list is a great signal.
As a bonus, for anyone who’s read the classic Cialdini book on this, asking for help counterintuitively brings you closer to others — and there’s a recommended formula for structuring your ask.
Tip #5. Make it fun!
Lastly, I recommend you find a way to have fun in this process – even if it means hacking the process a bit.
For those that are naturally extroverted and who love talking to investors, this doesn’t apply – you’re likely doing it already.
But for those who find this type of work a chore, I’d recommend you do two things.
First, hack your mindset.
While running a startup a few years ago, I complained to a founder friend about the time-consuming and frustrating nature of hiring- and he responded in a way that drastically shifted my mindset. He said he always viewed both the hiring process and investor dating process as “shopping” – a chance to meet and interact with a bunch of new people, see the variety of ways people approach solving the same challenges, and ultimately, enjoy the process of being in the driver’s seat to make the purchase you want.
Shift your mindset to one of shopping, or speed dating — knowing there will be many people that aren’t a fit but nevertheless, you could enjoy getting to know and learning something from. You’ll also likely continue to cross paths with many you meet.
Second, hack your habits. If you’re struggling with following through, I’d recommend you read Atomic Habits to set habits that are easy to follow, obvious, and trigger joy.
Ultimately, looking ahead toward your Series A and B, cultivating your next set of investors and advisors is a worthy investment to make, and one that doesn’t necessarily need to be painful or unduly time consuming.
If you’re running an early stage startup I’d love to talk and help where I can. You can reach me at firstname.lastname@example.org. I focus on Seed+, Series A and B companies, in all industries, with a special interest in fintech, enterprise, and B2B SaaS.