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Angel Investing 101 With Kira Jackson

Angel Investing 101 With Kira Jackson

Today on the blog we are welcoming SUCH badass, go-getter. Like you guys don’t even know.

Kira Jackson is smart as a whip, a marketing & PR whiz, & killer business woman, who also can add top-notch investor to her resumé.

We are so proud to have her on the blog to talk all about angel investing. Angel investing is defined as: a person who invests his or her own money into a company (usually a start-up), most commonly for an ownerships take as the investment is unsecured and the investor has no claim on the company’s assets.

So if you’ve got some extra cash floating around, and you’re looking to invest in a company you love, this post is for you.

With that, let’s get right into it with Kira.

Angel Investing 101 With Kira Jackson


Raise your hand if you remember being told by your math teacher that you’re “just not good at numbers.” Same. I convinced myself for years that I’d never *get* finance, and it’d be better to have my dad do my taxes anyway. So it’s kinda crazy to think that after all this time, here I am, working in Private Equity of all industries. 

Angel Investing 101 With Kira Jackson
Kira Jackson investing tips

Let me rewind a bit to recap my professional career thus far – from PR to PE (private equity) if you will. 

I started my career in PR as the second employee at a boutique agency called Covet PR, where I managed accounts like Suja, Kopari, Kashi, etc. I spent about eight years with the company. And as an early employee, had the opportunity to open our LA office, build out a new influencer and affiliate marketing department, and ultimately sell the company to an acquiring performance marketing agency. 

I stayed with Covet through the transition, and moved into a VP role, overseeing holistic marketing strategy for some of my favorite brands in the process – think SmartSweets, Bondi Sands, Florence by Mills, Winc… the list goes on. In that role, we scaled the firm from 150 to 500. And when the time came to bring on a new $$ sponsor for the business, I was selected among the dozen or so senior management leads who would be responsible for supporting in that process. This was my first brush with private equity, investment banking, and the world of finance in general. 

Kira Jackson profile
Angel Investing 101

When I tell you I learned more in those months than I had in years, I’m not exaggerating.

I had gotten to the stage with marketing where I felt I could probably do it in my sleep. The platforms changed (print > digital, Insta > TikTok, earned > affiliate, etc.), but the process didn’t. Investing and finance was a whole new ballgame. I started seeing businesses as full entities – I could not only understand their positioning strategy, marketing approach, and CAC/LTV ratio, but I could now spot inefficiencies in their manufacturing or supply chain, equity wasted on the wrong celebrity partner, IP or trademarks that strengthened the business, gaps in their team structure, and more.

All of a sudden, I understood the ins and outs of what made businesses successful. And because I’d spent ten years in the consumer space building brands, my network funneled me into a smooth transition onto the buy-side post-sale, which is where I sit currently, with a firm called RX3 Growth Partners.  

Kira Jackson on TSC
Kira Jackson on investing

High level, RX3 invests in consumer brands that are at their growth stage inflection points. Meaning, they are funded, likely on the path to profitability if not already, and have a solid product market fit with trajectory to scale and ultimately, exit.

We put money into businesses we believe in, and help them grow.

The firm was co-founded by Aaron Rodgers of the Green Bay Packers, and we count a number of celebrities, athletes, and influencers as investors – think Vanessa Hudgens, Kevin Hart, etc., so a lot of our value to portfolio companies is strategic connections to those investors, in addition to operating expertise – specifically mine in marketing.

Basically, I sit in a really cool, unique role where I straddle our deal and operating teams – supporting with bringing in new potential investments, evaluating those opportunities, and then helping our portfolio companies (the ones that we do invest in), grow.

Separate to RX3, I also angel invest and advise earlier stage businesses, which is what we’re going to dig into here.

Kira Jackson on the skinny confidential
How to Invest In or Advise Brands

All this to say, you genuinely can do anything that interests you. Your prior experience will make itself relevant, and will differentiate your perspective, making you all the more valuable!

Anyways. I digress. Let’s get into the nuts and bolts of angel investing and brand advisory.

♡ How to Invest In or Advise Brands

Getting deal flow and joining cap tables.

+ Network.

I know firsthand how anxiety-inducing it is when people say this, so I’ll clarify – I don’t mean forcing yourself to go to every event, talk to every human, and get straight to business. I actually kind of mean the opposite. You’ll get much more out of your network if you build it thoughtfully and with intention. Network with the people you naturally gravitate towards, then meet the people they naturally gravitated towards. Oh and most importantly, instead of asking for things, leave every conversation with a way you can provide value to them. Your network will quickly start thinking of you as the go-to problem solver / connector. And will start offering opportunities to you as a result.

+ Be passionate

Be passionate about what you do and the value you bring. In every conversation (whether you think an opportunity could come out of it or not), show just how excited you are about your expertise. Whether it’s your high-converting UGC, your pop culture know-all, your PR experience, etc., don’t be afraid to speak passionately and have an opinion about what you do.

+ Be honest.

Along the way, brands will ask for your opinion and perspective. In my case, many would ask for agency recommendations, or if I thought a partnership was worth a certain budget. Be respectful of course. But don’t be afraid to tell them the truth, *especially* if it’s something they wouldn’t expect you to say. This is where you gain their trust.

Behave gummy bears
mini doughnut

♡ How to evaluate a deal

So you got offered equity. Now, let’s make sure it’s worth it (bc you’re investing to make money, duh)! 

+ Do you get along with the team?

Whether you’re investing money or your time, you’re going to be a) spending a lot of time chatting with the brand team, and b) likely sticking your neck out for them. Are they people you trust to work their asses off and propel the business forward? Are they trustworthy and worthy of introductions to the people you worked really hard to earn their trust? Finally, are they the type of people that will value your input and/or jump into brainstorming sessions with you when the going gets tough?

+ Is the product differentiated?

It could be innovative or inventive, but is it unique, and is there a moat in place that will protect the brand from competitors?

Behave sour bears

+ What is the addressable market the brand is servicing?

In other words, are there enough people who want / need the brand’s products.

+ Evaluate the company’s striategy

Evaluate the company’s strategy in relation to emerging consumer behavior trends, because you won’t have many metrics to go off of. And you likely won’t have the historical data to be able to gauge the levers to pull to better unit economics or distribution yet. For instance, if a brand is launching now and planning to be fully DTC (direct-to-consumer) with the majority of their budget going toward paid social ads, I’d say run. The days of scaling a business through Facebook/IG are behind us. And data is indicating an impending shift toward an omnichannel approach. The same goes for price point (a luxury product will have a smaller TAM than a mass product. And as we enter a possible recession, you should ask yourself how the brand’s sell-through may be affected), market saturation (no one is asking for another celebrity beauty brand right now), etc.

+ Finally, I personally only invest in or get involved with brands that I use and love. If I’m putting my name on it, it has to be something that I authentically am obsessed with.

Behave sour bears marketing

♡ How to provide value

Ok, you made it on the cap table. Congrats! What’s next?

+ Ask the brand

Ask the brand what you can do to support. Every company is going to have different needs at different times. By the point of you actually accepting equity, you’ve probably already chatted with the Founder(s) about what they are looking for from you, but this will vary over the life cycle of the business. Maybe in the beginning the task will be to find other like-minded angel investors from your network to round out a fundraise. Maybe then they’ll be looking for you to send out a mailer of product to your friends and family to help extend brand visibility and awareness. And maybe they’d like to be included in upcoming events you’re hosting or are connected to. Be proactive about having the conversation upfront instead of guessing or just being a silent partner.

glonuts marketing

+ If you see something going wrong, speak up.

I know firsthand how difficult this can be, but you were brought onto the cap table for your expertise. So if you’ve seen something done more efficiently, or notice someone on the team isn’t performing the way they should be, etc., share your thoughts in a respectful manner, and provide recommendations and solutions.

+ Celebrate their wins.

Founders rarely get a chance to sit back and recognize something incredible. So if one of your companies gets into Whole Foods, or a Kardashian posts about them on social, etc., send cookies or a bottle of champagne! It’s the little things!

Angel Investing 101 With Kira Jackson
Angel Investing 101 With Kira Jackson

So curious to hear what you guys think about investing, and if there are any brands you have your eye on that you’d die to get in with! I’m always on the lookout for cool companies, and the people that can and want to help them grow, so feel free to hit me up on IG @kiramackenzie or TikTok @kiramackenz with tips and q’s about investing!



If you loved this post, you’ll love the HOT MINUTE PLANNER. It helps you run your day instead of the day running you. Be sure to stalk it here.

x, The Skinny Confidential team.

+ for more on investing & finance, check out this podcast episode.

++ & for some money saving tips, stalk this post by Nicole Lapin.


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