
Bootstrappers For Entrepreneurs · 2024-06-04 · 15 min
Key moments - from our scoring
Substance score
27 / 100
Five dimensions, 20 points each
Gwen and Jeremy Aspen of Aniquim explore how entrepreneurs can leverage in-person events as a core business development tool. The conversation moves beyond event logistics to address the psychological barriers - fear of poor attendance, rejection, and failed execution - that prevent most business owners from hosting regularly. They share practical frameworks: systematizing events through advance scheduling (like their Entrepreneurs' Organization model of four annual events), using the same vendors and planners, and integrating events into CRM strategy to maintain relationships. Key examples include Strata's IMN party strategy (high-profile photography for post-event content leverage), a Congressman's annual 4th of July gathering as a power-play networking tool, and personal stories of event failures that ultimately built confidence. The hosts argue that successful business operators treat their social calendar strategically, using events to bond current clients with prospects, showcase employees, and generate long-term marketing content. For property management firms, virtual assistant agencies, and service businesses, events become recruiting and closing tools when systematized with discipline.
Most entrepreneurs experience event anxiety rooted in fear of rejection (low attendance), fear of boring guests, or past failures; they expect to execute perfectly without practice, unlike other skills that are learned iteratively.
Schedule multiple events annually in advance, use the same event planner and vendors each time, integrate event invitations into your CRM, and follow up with calls to attendees - turning events into clockwork operations rather than one-off projects.
Professional photography and strategic social media use of event photos create months of post-event marketing value; birthdays of attendees become opportunities for personalized posts, amplifying the relationship-building impact long after the event.
Track attendee lists by relationship tier (friends, clients, prospects, employees), schedule events to hit all relationship groups throughout the year, and use the CRM to send personalized follow-ups - avoiding generic automated birthday emails that feel impersonal.
Never photograph yourself holding alcohol, beer, or cigarettes if you plan to use the images for business marketing, as it undermines the authority and professionalism you're trying to project.
Our reviewer’s read on each dimension, with quotes from the episode.
A small handful of actionable ideas exist - scheduling four events annually in advance, systematizing vendor relationships, and leveraging post-event photos for ongoing social media - but they are heavily diluted by personal anecdotes, tangential stories, and platitudes. The insight-to-filler ratio is poor for a 15-minute episode.
for entrepreneurs organization, we have the discipline that just have four events that we organize and schedule a year in advance
the second part of a party, it's not just the party, but it's the pictures you have from the party that you can post on the internet
The episode recycles conventional networking wisdom - events build relationships, relationships build business - with minimal fresh framing. The 'don't be photographed with alcohol' tip and the post-event birthday photo tactic are marginally novel but the rest is generic advice found in any networking book.
always put the alcohol aside when you're taking a picture that is an old political move that we learned a long time ago
in business is all about relationships. So the more parties that you have and the more relationships you build, the bigger your network is going to be
The hosts are genuine operators who have run a remote-staffing company and have direct experience organizing business events, which gives them practitioner credibility. However, there are no external guests, and the episode leans heavily on personal anecdote rather than demonstrating deep, transferable expertise at scale.
I'm Gwen Aspen with my business partner and spouse Jeremy Aspen of Aniquim, where we've helped hundreds of businesses scale with remote teams
I was membership chair so I in charge of these events
A few named entities appear - IMN conferences, Strata's party strategy, and a vague reference to a former Omaha congressman - but there are no metrics, dollar figures, conversion rates, or concrete outcomes attached to any of them. Anecdotes dominate over evidence.
there's this guy who goes to IMN conferences and his company is Strata. And he has a Strata event, which is known as like the late night crazy party at IMN
Congressman and mayor of Omaha. And he has this 4th of July party
The co-hosted format produces meandering, free-associative conversation with no sharp questions, no probing follow-ups, and extended detours into irrelevant personal stories (the pot roast dinner, the snake charmer). Neither host challenges the other or demands specifics, and the episode never recovers a coherent throughline.
I made a pot roast and I had just gotten a pot roast. Like who makes pot roast for a dinner party?
she was not really beautiful anymore she was not really and she came with a tiny snake so it was not the same experience
Computed from the transcript - who did the talking, and the words that came up most.
What is the true value of an event in today's digital world? The strategic value goes far beyond the execution of the event itself. In this episode, we'll cover the mindset shift event planning requires from the discipline and routine it gives you to the post promotion value in the content you get from it. Learn how events can be a catalyst for business growth, networking, and personal branding. Overcome your fear of hosting with tips from our experiences hosting successful (and challenging) events. Plus, discover the post-event benefits like content creation and community engagement, illustrating how events go beyond mere gatherings to become pivotal business strategies. Learn from their experiences of hosting a mix of successful and challenging events, and gain tips on making your next event a catalyst for business opportunities and stronger relationships. See how Anequim's virtual remote assistants are the solution to planning events for your business. This podcast is
Transcribed and scored by The B2B Podcast Index.
What is the true value of an event in today's digital world? The strategic value goes far beyond the execution of the event itself. In this episode, we'll cover the mindset shift event planning requires from the discipline and routine it gives you to the post-promotion value in the content you get from it. Welcome back to Bootstrappers, a podcast that helps you grow your business with remote professionals.
I'm Gwen Aspen with my business partner and spouse Jeremy Aspen of Aniquim, where we've helped hundreds of businesses scale with remote teams. All right. Today we're talking about the power of having events, like in-person events in your local community and how they can drive sales and relationships and the positives and negatives of these events. So this kind of came up because we had a huge event for us, a very formal dinner in December with some strategic people at our house.
And it was one of those events. I've had a lot of events in the past with mixed results. I think events are really terrifying because if you have a bad one, you're like scared to ever have another event. It's one of those things.
It's one of my phobias. Yeah, it's a phobia for a lot of people is having bad events. But I really am a believer that it's one of those things where we kind of feel like you should know how to do it without practice. For whatever reason, it falls into those categories of like, duh, you don't know how to have an event.
I don't know why. Well, I think the phobia is probably people not coming. Like that's nerve wracking. Which is a version of rejection.
Yes. I think that that is. Yeah, that's scary. It is.
And rejection is one of like the core fears of all people. Yeah. The other problem is just that like looking at people's faces and them having a boring, horrible time also. I've actually never been in a room where anybody was bored.
Yeah, right. Once you have a bad event though, you're like, well, I had an event that sucked and I survived. So I'll tell you a event. I think, Jeremy, you actually had fun, but I had a surprise birthday party for your 50th birthday.
And the event space was big because it was COVID. And I was like, oh, my God, I don't want people to get sick at an indoor event. But then when you had the event and it was too big of a space, it just looked bad. And then also, so it was a Halloween party.
And I wanted to have, like, crazy entertainment. so I got a snake charmer and I had seen her like I don't know 10 years ahead like 10 years earlier and she had this huge snake and she was really beautiful and then she came back and she was not really beautiful anymore she was not really and she came with a tiny snake so it was not the same experience that we had had the first time we had seen her perform at all and so that left a lot to be desired. Oh, that was fun. But yeah.
You still had fun, but like as far as an event goes, it was not my best, not my best event. But, and I had thought about that like years later about being embarrassed about that event. I actually, it's something I think about. But since then we had a great event for this Christmas party and that went on without a hitch.
And like for entrepreneurs organization, we have the discipline that just have four events that we organize and schedule a year in advance And then we always have something to invite people to And that works as our recruiting event And I really after being an entrepreneur organization I membership chair so I in charge of these events. And really, they're very simple. We have speakers anyway. And then we just get the same, we have the same event planner as who's managing the speaking event.
And then we have an add-on cocktail party. We have the same vendors for food and drink. And it's just like clockwork and it works. And then the only really hard part is getting people to that event, which once you have it systematized, isn't even that hard.
You just have people's names and your CRM and then you have an invite and then you just send the invite and you follow up and you have an excuse to call people also. And probably worth mentioning is how does this apply to property management or some of the other industries that hire virtual assistants or remote professionals. I remember when we had just moved to a new office, I think a couple of times we did this, we would have social events. And we did try to do it a couple of times.
Well, we tried to do it. We thought, oh, this is a great idea. Let's regularly do it. And it just fizzled because we didn't have the...
Discipline behind it. It probably wasn't the discipline. And also nobody wanted to do it. Nobody wanted to set everything up because especially because it's so stressful but always it's worth doing because you you bring your current clients you bring some potential clients you get your the clients that showed up like you talking to potential clients that makes them much more likelihood of being able to close a deal it plus not to mention that you're bonding and you're getting to know each other and your maintenance technicians are you know selling for you yeah and then you get to watch them shine and do a great job.
They get to get drunk out of their mind. No, no, not true. And so, yes. And then everybody feels like really good about the business.
And it's also promotes positivity in the employees as well. So, so it's a win-win all the way around. I just want to mention a few other people who are really good at events. One is there's this guy who goes to IMN conferences and his company is Strata.
And he has a Strata event, which is known as like the late night crazy party at IMN. And he doesn't have a booth. All he does is host a party and he has a great photographer so that he can have those pictures live on on the internet. Because the second part of a party, it's not just the party, but it's the pictures you have from the party that you can post on the internet.
So it builds kind of like your prestige. It builds your, I don't know, like you're, you're like the cool person in the room. Yeah. Your cachet.
I would say don't take pictures with you having alcohol in your hand or mouth. That is a, that is a good idea. Yeah. You know, always put the alcohol.
No beer bombs or bongs. always put the alcohol aside when you're taking a picture that is an old political move that we learned a long time ago yeah especially if there's going to be like if you're going to use it for your future marketing stuff like that you know holding a cigarette and a bud light just doesn't it's not it doesn't it doesn't have the authority that the authority it might be looking for but if you have these pictures and then i've seen other people who are super good at social media even get more use out of the photos by if they make sure that they're at an event, they get pictures of everybody, they get pictures of them with everyone.
Then when it that person birthday they post a birthday post about that person with that photograph way after the event And it the gift that keeps on giving Yeah. And it really is just the discipline. It's really having like a process for parties or a process for conventions or a process where you just this is part of your process and you make it happen. And the most successful people I've seen in business or politics are really good at processing events.
So we do have like a past, he was a senator, right? A senator. No, but yeah. Congressman.
Yeah. Congressman and mayor of Omaha. And he has this 4th of July party. And you know if you're on his good side, if you get invited.
And you know if you're on his bad side because you are not invited. Yeah, that happens. And it's like the who's who of Omaha and Nebraska. Politics, yeah, it is.
And it is a fun party to go to just knowing that, oh, there's the governor and there's all the senators and there's all the congressmen. And it's really a neat gig. But it comes at a price. Toe the line.
Like, yes. If you don't toe the line, you're not going. We're not invited anymore. We're not invited anymore.
But we used to be invited and we used to care about being invited. And I remember being like, oh, my God, the 4th of July is coming. Did we make the cut? Did we piss him off?
I never gave any shits about whether or not we did. I just thought it was interesting because it was like such a power dynamic. It was a power play. It was a major power play.
And you knew you weren't invited because you knew that they were going to have - they had that party every year. It was part of their process. Oh, yeah. It was - yeah, it was annualized.
And I guarantee you, he and his wife would get together and say, okay, yes, no, yes, no, yes, no, through the whole list. And it was based on whether or not you'd written something bad about some of their elected officials in the paper. It was a move. It was a move.
He's deliberate. And it is the power also of just having a good CRM system. Because I know he's pretty old. So I'm sure his was on paper.
Oh, I guarantee you it was on paper. But the new CRM systems, the people who I've noticed are really good at business. They probably have their personal list in a CRM and they prioritize relationships with certain people. Like they'll have a party for their high school friends and then they'll have a party for their business contacts.
And they kind of think through their social life and their social engagements and the parties that they have and the vacations they go on in a strategic way so that they hit all the people that are important in their life and as well hit maybe some of the good business contacts as they're organizing their schedule. And then they kind of design their social life in a way where it's like important to them and take the time to do that. And I always really admire, I'm not that person, but I really do admire people who are that organized about their personal life.
Well, and if you think about if you've ever been invited to, you know, philanthropic events or anything, that's the that's what's going on in the background always. I mean, and it's you know, there's I think there's a risk. Like if you're tracking somebody's birthday and you send them a goddamn email, it says happy birthday or it's not personal. Yeah, it just that's a waste of time because it you look at it.
Now, if you say something like, oh, remember that one time we were at this one place and it's personalized? Okay. But CRMs all have that They all send out automated emails It for me it actually an insult I don like that Your insurance agent remembered your birthday Yeah. With, with something that they, you know, in January, they all got together and signed all of these 5,226 cards with their little, no kidding signatures like this long and this short.
I mean, it's just, it's just does, it's just not genuine. It has to be genuine. And that's what parties get you to do. I mean, you know, if you're ever invited to a party, lest you fear that you might be being used.
The nice thing about being invited to a party is that it's because you're a part of them. Like you'd be a good mix. You don't just invite assholes to a party. You're not going to a party if you're, if you're not going to bring to it.
So it's, it's a nice way to keep the kind of the energy going, people trusting you and you trusting them and, and doing it in a methodical way. Not a bad idea. To get easier, I mean, when I was 23 and we started having parties, like one of our first marriage stories is about a terrible dinner party that we had. When you caused a divorce.
And that was like, I was like 23 and really stupid and didn't know anything. And I made a pot roast and I had just gotten a pot roast. Like who makes pot roast for a dinner party? and we had just gotten a slow cooker and it was like the first time I'd ever used one.
And I'm like, it has a high setting. Why would you use a low setting when there's a high setting? Beef jerky. You can make the spot roast three hours earlier.
Well, we found out, I found it, my 23 year old dumb self found out very quickly why there's a high setting and a low setting, why you never use the high setting and not eat that meat if your life depended on it. And then she accidentally told one of the women there that her other half. Not better half. Well, he's my friend.
He wasn't perfectly faithful. Yeah. Well, we thought they were on a break. I thought it was like a friends episode where I felt like Ross, I thought you were on a break.
But anyway, I spilled the beans that he had hooked up with my roommate when I lived in Kansas City and that didn't go well. And so anyway, my very first dinner party was a complete disaster. But you know what? You live and learn.
And if you have parties and they fail, you're going to survive. And they're so helpful in networking, in getting invited to parties. Like if you have parties, you'll get invited to parties most likely. And in business is all about relationships.
So the more parties that you have and the more relationships you build, the bigger your network is going to be and the more successful you're going to be. So I just encourage you, have a party, put yourself out there, risk rejection, risk failure. It will help in the long run and it gets easier the more you systematize it over time. and you can start small and get bigger.
It really does improve sales and the success of a business. Transform your event planning with Antiquim's remote professionals. From logistics to marketing, our virtual assistants help you maximize your event's value, freeing you up to focus on big picture strategies. Antiquim ensures your event leverages every opportunity for growth, networking, and content creation.
Contact Adequim today and let our experts elevate your approach to event planning for impactful business advancement.