I’m Sam. I run a company called Tripler AI; It's my fourth business.

My first company was a marketing services business. It was also my first exit. I thought I wouldn't do anything again, but that lasted about a year. 

My second company was in the hospitality space. I did my first project and then we got an investor, a US private equity fund run by Sam Zell.

Then I started a real estate transaction business called India Homes. I ended up selling that company to a London Stock Exchange-listed marketing group.

Now my fourth company, Tripler AI, is an AI company focused on real estate. I've raised capital from 5 pre-seed investors and in a couple months will get my seed done.

For the marketing services company back in 1998-1999, I raised $2M at a $10M valuation. 

At the hospitality company, I raised $10M at a $50M valuation prior to the exit. 

From India Homes, we raised multiple rounds (Seed, Series A, Series B). The peak valuation was $160M. 

For Tripler AI, we’re now at the seed stage. The pre-seed was about $15M.

For Tripler AI, the capital is going to be used to scale.

The best way to think about the business is similar to Uber. It's going to be in the city, so you've got to add a hub. The capital will get the engine working in a new market.

Different companies raise capital at different stages of their evolution. Always optimize for deal certainty over valuation. 

Valuation is really just a vanity metric at that point anyway, it's just numbers on a piece of paper.

I did what I internally called “no-deal roadshows.” 

I would go up to successful people through networks and contacts, or just meet them at events and say that I have this company and I'm not pitching you for capital, but this is what I'm up to. 

I tell them upfront that I'm not looking for capital. 

Every time that I've received capital, I've gone in saying that I wasn’t looking for capital. 

Those ‘no deal roadshows’ would end up in connections, which would over a period of time, mature into investment transactions.

I was very lucky a couple of times. 

For the India Homes company, when we raised from Foundation Capital, we didn't go anywhere. They came to us because the fundamentals were working.

You have an unfair advantage when you’ve raised capital before and have a couple of exits behind you. There’s less founder-risk for the investor.

I was able to approach it with a sense of confidence as a result and cut through who's going to be serious relatively early on.

The forcing function was highlighting how it was actually less beneficial for the investor the longer I had my eyes off running the business (and on fundraising instead).

That kind of candor helped push urgency. Always just be candid and say, “you're screwing the business that you're looking to invest in if you make this a laborious process.”

Trying to raise from people who've never run a successful startup.

No matter how many years out of HBS you are, and no matter how much time you spent at Goldman Sachs, that is not the same thing as running a startup. 

In the typical VC model, there are associates who don't have any idea what to look for; they're operating off a spreadsheet. It's a filter that doesn't know what to filter.

Another challenge is the fact that you need the capital faster than the investor needs to give it to you. The asymmetry of power and urgency can be a huge issue.

For India Homes, I seed funded that with friends and family. 

We then raised our Series A from Foundation Capital. I turned down a term sheet from Sequoia to do that.

We then did a Series B. A large VC funded a competitor off the back of a business plan and wrote them a $100M check to beat us. 

The competitor then started out spending us on customer acquisition.

I told the lead investor on the board that it wasn’t a battle worth having because the competitor was going to run out of money. My plan was to wait it out, but ultimately that’s not what happened. 

Our lead decided to write bigger checks and I decided to leave. After I left, the lead investor brought in the CEO of Vodafone India to run my startup. 

They eventually had to restructure and do a distressed sale of the business.

Don’t pretend you have product-market fit when you’re fundraising if you haven’t found it yet. You’re screwing yourself by giving away all the leverage. 

The guy who has the checkbook effectively runs the business.

Valuation is the least of your problems early on. It's more about your chemistry with investors. 

If they're going to make things hard for you and not understand that every month is an existential threat, then that's not the right partner you want anyway.

There's a science to timing the ask for investment. If you ask too early, it's a no. If you ask too late, it doesn't work. 

The intuitive science around timing of the ask for investment can make all the difference.

Take capital wherever you get it from, even if it’s from someone who doesn’t know what they’re doing. It’s disrespectful to say no to capital.

If you're raising money and it's OPM (other people's money), you have to ensure that you can use it to amplify what's already working rather than to try and use it to find something that works. 

Mohit Bhatnagar from Sequoia India is amazing. He's a great guy and he’s very supportive. 

Jack Azout from Elyon Partners. He's a super solid investor to have on board early on.

Houck’s Newsletter!

Also, for a first time founder, sign up with a lot of these companies that claim to train you. Even though they won't deliver on what they say, the 10-20% they do move you along has value.

There's a company called Established PR that nurtures and grooms your pitch quite well. Foundational NYC is good too.