I'm Jared Kleinert, Founder and CEO of Offsite. Offsite is Airbnb for team retreats. 

We’ve raised a total of $4.3M to date, but the journey hasn’t been linear. We initially took investment from Forum Ventures back in 2021, on standard accelerator terms (7.5% for $100K).

Later that year, we raised a pre-seed round mostly from angel investors—nearly 70 of them. Many were notable CEOs, and we even had customers and marketing partners who wanted to invest.

We went out to raise our seed round in April 2022, which turned out to be the worst possible timing with the VC market crashing. We had opted to skip Forum’s October 2021 investor showcase and joined the April 2022 one instead.

Ultimately, we pieced together a number of SAFEs over the summer: $500K from Forum Ventures, $500K from Automattic’s corporate venture arm, and a few additional angel checks.

That all converted into a priced round when we took in another $1M in April 2023. We’re now doing a seed extension—not because we need the money (we hit breakeven this quarter), but to invest in growth for 2025 and prepare for a larger Series A at the end of 2025 or early 2026.

Most of our fundraising has gone toward growth. With the seed extension, we’re using some funds for strategic hires, but we’re also increasing variable spend across marketing and advertising.

In the past, we made the mistake of hiring too quickly. Just because you raise money doesn’t mean you need to spend it immediately. You want the capital to last longer than expected, and ideally, raise when your numbers are strong.

When you’re confident that bringing in new capital can generate positive returns for all stakeholders, then it’s worth the dilution.

We have a pretty unique business model as a marketplace. When it comes to fundraising, it takes a certain kind of investor to believe in the various business models that we have. 

Some investors love backing marketplaces and understand the possible brand moats and other marketplace dynamics that can lead to a lot of defensibility.

But it is potentially capital intensive to build a marketplace and it takes a while. It's different from SaaS and other business models that a lot of VCs love. 

On that point alone, some investors will pass while others get super excited. Another polarizing point is the future workplace — we're a fully remote team,

We are a service that all companies can use, but remote first or hybrid teams find more value in what we offer, as would a distributed team.

If you're a VC that believes in office work and or you believe that the future work will be returned to the office, then one might be polarized for or against what we're doing as well. 

We also have a tech-enabled service part of the business. It makes us really capital efficient, teaches us what software to build, and it creates a lot of great affinity with our customers.

But you have to be a certain type of VC to buy into the vision that our service will be increasingly tech-enabled and will have an increasingly higher margin. 

Because of all this, we cast a wide net. Funds have different ownership targets and different structures. Some funds would rather wait until a Series A, other funds were too late because we've given up too much of the company for them to reach those ownership targets.

Most of our more successful conversations came from direct introductions from other founders or from other investors. Networking and relationship building is the name of the game. We did a lot of cold emailing as well. 

For the seed extension, we reached out to over 200 funds—via cold outreach, intros, or direct contact. We got 115 no’s, most of them without a meeting being booked.

The funds either simply weren't interested in the space, they weren't deploying capital, they didn't do seed extension rounds, etc. 

Out of that, I probably booked at least first calls with like around 40 funds. 3 or 4 funds ultimately ended up backing us.

We were fundraising because various parts of the business were flashing indicators that we should grow faster. 

While we were breakeven, and stressing those indicators and having our sights set on being a category-defining potentially billion dollar company in an exploding market was what we focused on. 

We also said that we would be able to use the capital to invest in growth and ultimately try and win the category.

I don't think FOMO works in 2024. The best way to drive urgency is to run a tight process like one does in sales and attempt to contact everyone at the same time so you get as many first meetings at the same time.

The goal is to arrive at the end of the process with multiple funds giving you a term sheet. That's the best way to drive urgency.

I thought we were going to get the fundraise done in about 6 weeks because we got close to having one fund do the Seed extension, if not 2 funds.

I ran the process and very quickly got to diligence with a couple of funds. I stopped building the pipeline and taking more meetings because I was confident the funds were going to participate. 

They had all the signs of ultimately backing a company, even having conversations with our customers and speaking to our board members and investors. 

The big learning lesson would be to continue building the pipeline and not actually trust that you're going to have people cross the finish line until it's actually done. 

That probably doubled the process. What could have been 6 weeks ended up being 10 weeks to get a term sheet and another couple weeks to get the wire done, which is still not bad.

One thing I'm planning to do is contact the next stage of investors and get a sense of the benchmarks that we would need to hit. 

So for us, that'd be a series A. I’ll contact the funds that we spoke to that said it's not for them right now, but would invest later on. 

There's also a whole bunch of funds that we didn't contact that tend to focus on Series A companies and beyond.

It’s helpful to do this for a couple of reasons. It’s most VCs' jobs to know what the benchmarks are and what the growth goals would be to see what a good investment might be. 

The second thing is that this becomes a relationship-building exercise and could hopefully make the next round easier if we're able to show that we executed a plan over a few months to a year.

Try to be as stoic about the process as possible. You’re going to hear a ton of no’s. It's almost entirely not personal. If it's personal, you probably have other issues. 

There's a million reasons why funds could say no, but you only need 1 or maybe 2 to help you unlock your next steps in the company by saying yes.

Don't get too excited about a call going well, but also don't get discouraged at any point in the journey. 

You have to treat every call like they could be your future partner because you never know which pitch will lead to the eventual partner.

I've had a great relationship with Forum Ventures. They have an accelerator program. They also have a Seed fund and they have a venture studio that they've invested a lot into. 

Especially if you're interested in building in the AI space, they're doing a lot of different companies where they're looking for a founder to come in but they have the idea in most cases and they're given capital and have a cool setup around that.

There's a book called 7 Powers by Hamilton Helmer that one of the co-founders at Invisible suggested I read.

It was really enlightening to talk through the different moats that you can develop. It was really helpful to think through which ones might apply to us. 

A lot of times, investors are thinking about defensibility. That book can give you some language as to what can be defensible and how you might get there. 

I’m also in a group called Hampton. My core group specifically, which is a small group of other CEOs that we meet with monthly, were helpful when I was crafting my pitch deck.

We've kept pretty reasonable valuations throughout. That's provided us with a lot of optionality. 

Unless you're willing to go big or go home and willing to do things like down rounds, I've learned to actually optimize for reasonable valuations with great partners rather than stretching for insane valuations that can make you really rich only if you are completely right.

Higher valuations can be good if you know how to play the game really well. 

But it's very hard to have the discipline and the market timing to turn really high valuations into the right outcomes for yourself.

You definitely have much more optionality along the way if you keep your valuations reasonable.